US2871145A - Process of impregnating textile material to increase its wear resistance - Google Patents
Process of impregnating textile material to increase its wear resistance Download PDFInfo
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- US2871145A US2871145A US431603A US43160354A US2871145A US 2871145 A US2871145 A US 2871145A US 431603 A US431603 A US 431603A US 43160354 A US43160354 A US 43160354A US 2871145 A US2871145 A US 2871145A
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- bath
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- textile
- emulsion
- formaldehyde
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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
- D06M13/12—Aldehydes; Ketones
- D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
Definitions
- This invention relates 'to"'the--treatmentof textile-materialssuch ⁇ as tthreadsyarns; 'fabrics and-knitted* goods, and morev particularly -to' f a 'process' of* -treating such materials to improve their'qualities and their mechanical properties, such as resistance.towear, and to a composition suitable for use in practising said process.
- This AapplicationN is-A alcontinuation-impart-lof priorl l applica- "tion Serial-No. -371-,11-89,-filed--onlJuly :29,11953, now
- Ythe process consists of an immersion of the textile successively vin a first bath 'made' up of* arrernulsion containing -atfleast-one plastic material, one 'plasticizing materialand possibly 'at least one'metallicsalt; then in a second-bath containing -aninsolubilizing reagent.
- United State tent ELST/LMS Patented Jan. 27, i959 /The .drawing discloses a low diagram illustrating the process of treating textile materials lin accordance with the present invention.
- the treatment so applied confers upon the textile prop- 5 etries .advantageous for the following reasons: the first bath phas ythe-'effect'of impregnating the textile with an emulsion of the plastic material and its vplasticizingagent together with otheragents which impler'nent this impregnation ⁇ by -their wetting action; the second bath has the effect of breaking ⁇ the emulsion and fixing the resin situin the fabric by precipitating the plastic materiallin an insoluble form within the interstices of the textile fibers.
- the plastic materialconternplatedby the ⁇ present invention is a material whichis" insoluble in water but is emulsiable therein and,i s hstableto organic acids.
- resinsnone will use :in .preference .thermo-plastic ,materials, usuch yas 4polyvinyls,lpolystyrene, acrylic resin,
- thermo-stable,materials such as aminoplast, synthetic rubber, rubber latex, etc.
- A. textile.product .which uis. particularly resistanttowashing is obtained by utilizing as the plastic material a mixn ture-ofitherrnoplastic resinsor thermo-Stable resins with 40 .proteins.
- the synthetic-resins ⁇ may Abe -plasticized in preparing them for the above mentioned use, andV for that purpose one may use fatty materials, i. e. long chainlcompounds, such'as parafiin, Vaseline, wax emulsions and similar hy- -drocarbondistillates, and-natural-wax emulsions.
- Vase- #line is-a-t-radem-arkV used bythe-Chesebrough Manufaclturing Gompany,-New-York, NewYork, for its petroleum jelly.
- v'It - may-befound advantageous tovadd wetting agents whenfthe product is being prepared, lthus permitting an -easierpenetration-of the interstices ofthe'bers VVby the product when it is applied to textiles.
- organic acids such as acetic acid.
- inongst metallicsalts one ⁇ will use in preference acid salts of aluminumna'nd zinc, suchasrborates'and silicates.
- such ak bath of emulsified resinsy is stable and may be used over a period of time without any appreciable change occurring in its chemical composition.
- resins proteins, plasticizers,. etc.
- parain emulsion or any resin emulsion, which appears in the following examples is to be understood to mean a stable, aqueous dispersion of paratiin or of the particular resin.
- the ratios of the ingredients used in the following examples of the composition of the first bath are givenv in parts by weight, while the ingredients which make up the second or rinsing bath are given in parts by volume.
- a composition for a stable first bath is produced by mixing together the following ingredients in the proportions listed, which are in parts by weight, and then: diluting the mixture with from l0 to 20 or more timesits volume with water.
- Polyvinyl chloride emulsion 45 Parain emulsion 45 Dry gelatin (steeped for 24 hours in water) 5 Sodium borate
- the textile to be treated is first steeped in this diluted bath, preferably at 30 C., is wrung out, and then directly steeped in a rinsing bath prepared by the user and which has the following composition:
- an equal quantity of aluminum acetate may be substituted for acetic acid in this rinsing bath.
- Sodium silicate may be substituted for the sodium borate in the composition of the first bath and comparable results would be achieved.
- first and second baths are illustrated infra with the composition of the concentrated mixture being diluted with water l0 to 20 or more times ,its volume. While baths diluted in a volume of water 10 times the volume of the composition gives satisfactory results, it has been noted that excellent results are obtained when the dilution is in the ratio of one volume of concentrated mixture to 20 volumes of water.
- a process of treating textile material to increase its wear resistance comprising the steps of steeping the textile material in a rst bath comprising an aqueous emulsion of an emulsiable resin, parain emulsion, and gelatin, and then steeping said treated textile in a second bath comprising formaldehyde and a member selected from the group consisting of acetic acid and aluminum acetate.
- a process ,of treating textile material to increase its wear resistance comprising the steps of steeping the textile material in a first bath comprising an aqueous emulsion of an emulsiable resin, a plasticizing component for said resin selected from the group consisting of parain, petroleum jelly, and wax, gelatin, and a member selected from the group ⁇ consisting of sodium borate and sodium silicate; and then steeping said treated textile in a second bath consisting of water, formaldehyde, and a member selected from the group consisting of acetic acid and aluminum acetate.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Jan. 27, 1959 J. HAJDU 2,871,145
PRocEss 0E IMPREGNATING TEXTILE MATERIAL To INCREASE ITS WEAR RESISTANCE Filed May v21, 1954 BYW/M@ ATTORNEYS .PROCESS t yoF nunREGNATmG .TEXTILE .MATE- RIAL ,.To. INCREASEQ IIS WEARIRESISTANCE xosepunaiduypris, France ....nppiicationMayizl, .1954,.smfa1 .N0. .431,603
/z claims. --(c1.117139;s)
This invention` relates 'to"'the--treatmentof textile-materialssuch^as tthreadsyarns; 'fabrics and-knitted* goods, and morev particularly -to' f a 'process' of* -treating such materials to improve their'qualities and their mechanical properties, such as resistance.towear, and to a composition suitable for use in practising said process. `This AapplicationN -is-A alcontinuation-impart-lof priorl l applica- "tion Serial-No. -371-,11-89,-filed--onlJuly :29,11953, now
abandoned Known-processes tow improve Ythequalities of textiles, -.i. e.,- their. resistance-towear -Ythrough i abrasion, their rubbingcoetlicient.,andtheirmechanical-propertiesl in general, present inherent drawbacks. In the rstplacaatheir y. application.. necessitates. .different stages. of... operation, C vwit, immersion. ,ofthe .textilaiu a :batmwringingithe texntile and drying it, l,all vof which stagesfhavelQsbexrepeated a numbertoftimes. Y.The:preparation ofthe various baths I`ist a very delicate operation, a small variationlinlhe coml.position ofthe bath resulting inafdiiferenueifecton the l.textile treated. Various processes permittingareduction in the number of baths have already been evolved but the products which went into the baths had the inconvenience of being very unstable and did not ,permita prolonged use of the bath. Furthermore, the omission of coating chemicals, indispensable to' achievefthe result aimedv at,'"hadV for directeie'ct'the' lossthrough' washing of'the qualitiesk acquired"during"'the treatment.
Results secured from 'the' known "treatments, though fairly" satisfactory, `did` not achieve" the necessarydegree ofi-perfection. YIn certain knownprocesses,"the' Vresult was a simple coating of some plastic matter on 'fthe-etextile, ywhich made. Ythe-textile rigid- --and evenbrittle. -iAnother i process...deposited-silica particles v on the# textile `-which made the. feel-of the fabric-less desirable, or; asV `in the case of a process with a lesser number of baths, the desiredeffect was -notflasting ,This inventionhas none.of.the.abovermentioned draw- Qbacksasitpermits thetreating ofatextilesithrough a reduced.. number.. of .baths and results; in; at textile i which presents the'qualities most sought after and, at the same time, permits the productiorrcfja concentrated mixture perfectly homogeneous and stable, and which afterfsirnple dilution may be very easily appliedgtOftheytextile.
It is accordingly an object of the, presentginvention to provide a newand improved processpof treatingggtextile materials to improve their. qualities and ,their mechanical ,s properties in general. v
It is another o bject of the present@inxentionftoprovide such a process whereby itis possible tosubstantially increase the resistance to wear of a textile material.
. It is a further object of the present inventionzto, provide a new and improved composition for use y,insuclr aprocess. According to a preferred embodimentgofjthe.present invention, Ythe process consists of an immersion of the textile successively vin a first bath 'made' up of* arrernulsion containing -atfleast-one plastic material, one 'plasticizing materialand possibly 'at least one'metallicsalt; then in a second-bath containing -aninsolubilizing reagent.
United State tent ELST/LMS Patented Jan. 27, i959 /The .drawing discloses a low diagram illustrating the process of treating textile materials lin accordance with the present invention.
The treatment so applied confers upon the textile prop- 5 etries .advantageous for the following reasons: the first bath phas ythe-'effect'of impregnating the textile with an emulsion of the plastic material and its vplasticizingagent together with otheragents which impler'nent this impregnation `by -their wetting action; the second bath has the effect of breaking `the emulsion and fixing the resin situin the fabric by precipitating the plastic materiallin an insoluble form within the interstices of the textile fibers. These insolubilized particles are perfectly resistant to washingbesidesbein'g supple and smooth, and thus diminish the eifect vof the rubbing together of the bers-by permitting the-sliding ofthe bers internallyin the manner of vball bearings employed in mechanical constructions. In this way, yinstead of a coating of plastic material upon the surface of the textile, thereis an impregnationof thebers'lby the plastic `material particles which renders the -textile soft, improves its feel and, what is mostimportant, lincreases its resistance to wear.
'The plastic materialconternplatedby the `present invention is a material whichis" insoluble in water but is emulsiable therein and,i s hstableto organic acids. One
can use, for example, as such plastic material any synithetimor-:natural 1resin.in.a. liquid medium. .Amongst synthetic ,resinsnone will use :in .preference .thermo-plastic ,materials, usuch yas 4polyvinyls,lpolystyrene, acrylic resin,
fzmethylnrnethacrylate or thermo-stable,materials,.,such as aminoplast, synthetic rubber, rubber latex, etc.
Amongst natural resins, one will use in preferencer those which can form an insoluble compositeY with aldehydes'for r'formaldehydesxar.acids, asffor example, naturalproteins Lsuch -`as Ngelatinycasein, .egg albumin, `blood-albumin,
-ialg-inatesfetc. f
A. textile.product .which uis. particularly resistanttowashing is obtained by utilizing as the plastic material a mixn ture-ofitherrnoplastic resinsor thermo-Stable resins with 40 .proteins.
"The synthetic-resins `may Abe -plasticized in preparing them for the above mentioned use, andV for that purpose one may use fatty materials, i. e. long chainlcompounds, such'as parafiin, Vaseline, wax emulsions and similar hy- -drocarbondistillates, and-natural-wax emulsions. Vase- #line is-a-t-radem-arkV used bythe-Chesebrough Manufaclturing Gompany,-New-York, NewYork, for its petroleum jelly.
v'It -may-befound advantageous tovadd wetting agents whenfthe product is being prepared, lthus permitting an -easierpenetration-of the interstices ofthe'bers VVby the product when it is applied to textiles. Bases or alkaline salts may also be added, which will act rst as stabilizers forthe emulsions, thenwill facilitate their decomposi- `=tionand insolubilization when the product is diluted.
lo precipitate and insolubilize the product once it lhas-beendiluted, one can use: i
5(1) Acids or metallic salts to startv the precipitation.
(2) Aldehydes to insure insolubilization. i
Amongst acids, one Ywill use ,in preference organic acids, such as acetic acid. inongst metallicsalts, one `will use in preference acid salts of aluminumna'nd zinc, suchasrborates'and silicates. l'.[fheseorganic acids and jmetallicsaltsactuallybreak up the emulsion and cause theplastic-material-"particles within the intersticescf the textile-tibersto-be"precipitated thereon.V :If "one wishes jat -the `sametimetowaterproof the textile, thentiliza- "tionof'metallic 4salts inplace of vvthe organic',v acid .is ,advised r1"The-product."which-will constitute therst 'bath can f, be commercialized ina concentrated vform .and` is .diluted A'many times'its `volume-by Water when used, for example,
from l to 20 times or more, with the best results obtained when it is diluted with water 20 Atimes itsvolume. The user therefore has the means to reproduce exactly the same bath composition which will-give himthe. desired effect without having to handle large quantitiesof various liquids and compositions, as is the case' with other known processes. i
Furthermore, once prepared, such ak bath of emulsified resinsy is stable and may be used over a period of time without any appreciable change occurring in its chemical composition.
The preparation of the second bath which precipitatesy and insolubilizes lthe plastic particles. within the interstices of the textile fibersV presents no difficulty outside of mixing the ingredients in the parts by volume specified infra.
As specific examples of resins, proteins, plasticizers,. etc., suitable for the purposes of the present invention, the following are given merely for purposes of illustration and not in limitation. The term parain emulsion, or any resin emulsion, which appears in the following examples is to be understood to mean a stable, aqueous dispersion of paratiin or of the particular resin. The ratios of the ingredients used in the following examples of the composition of the first bath are givenv in parts by weight, while the ingredients which make up the second or rinsing bath are given in parts by volume.
Example N o. l
A composition for a stable first bath is produced by mixing together the following ingredients in the proportions listed, which are in parts by weight, and then: diluting the mixture with from l0 to 20 or more timesits volume with water.
First bath:
Polyvinyl chloride emulsion 45 Parain emulsion 45 Dry gelatin (steeped for 24 hours in water) 5 Sodium borate The textile to be treated is first steeped in this diluted bath, preferably at 30 C., is wrung out, and then directly steeped in a rinsing bath prepared by the user and which has the following composition:
Second bath:
Water 1000 Acetic acid Commercial formaldehyde 10 The textile is wrung out after its removal from the rinsing bath and dried at a temperature of 80 to 110 C. A textile thus treated has its mechanical properties modified as to increase its resistance to wear, and improve its rubbing coefficient.
If it is desired to also waterproof the textile, an equal quantity of aluminum acetate may be substituted for acetic acid in this rinsing bath.
Sodium silicate may be substituted for the sodium borate in the composition of the first bath and comparable results would be achieved.
Example No. 2
4 Second bath (for a water-repellent treatment):
Water 1000 Aluminum acetate 30 Formaldehyde l0 The product of the first bath is diluted with water 20 times its volume to form a stable solution and the textile or fabric is steeped therein at 30 C., wrung out vand then steeped in the second or rinsing bath. Dependving on whether the textile or fabric is to be made waterrepellent or not, one of the two examples of the second Vbath illustrated above may be used as the rinse bath.
Additional examples of first and second baths are illustrated infra with the composition of the concentrated mixture being diluted with water l0 to 20 or more times ,its volume. While baths diluted in a volume of water 10 times the volume of the composition gives satisfactory results, it has been noted that excellent results are obtained when the dilution is in the ratio of one volume of concentrated mixture to 20 volumes of water.
Example No. 3
First bath:
Parafn emulsion (concentrate) 45 Sodium alginate 10 Sodium silicate 5 Dry gelatin 1 Sodium fluosilicate 3 Water 36 Second bath:
Water 1000 Calcium chloride 40 Formaldehyde l0 Second bath (making the textiles water-repellent):
Water 1000 Aluminum acetate 30 Formaldehyde l0 Example No.`4
First bath:
Parain emulsion (concentrate) 45 Milk caseine 15 Sodium silicate 5 Gelatin 1 Sodium benzoate 3 Water 3l Second bath:
Water 1000 Acetic acid 10 Formaldehyde 10 Second bath (making the textiles water-repellent):
Water 1000 Aluminum acetate 30 Formaldehyde l0 Example No. 5
First bath:
Parain emulsion 45 Egg albumen 10 Sodium silicate 5 Gelatin l Sodium benzoate 3 Sodium uosilicate 1 Water 35 Second bath: v
Water 1000 Acetic acid l0 Formaldehyde 1() Second bath (making the textiles water-repellent):
Water 1000 Aluminum acetate 30 Formaldehyde y l0 5 Example No.y 6 First bath:
Parain emulsion 45 Blood albumen 15 Sodium silicate 5 Gelatin 1 Sodium benzoate 2 Sodium uosilicate 2 Water 30 Second bath:
Water 1000 Acetic acid 10 Formaldehyde 10 Second bath (making the textiles water-repellent):
Water 1000 Aluminum acetate 30 Formaldehyde 10 Example No. 7 First bath:
Paran emulsion (concentrated) 45 Methyl methacrylate emulsion 30 Sodium silicate 5 Gelatin l Sodium benzoate 2` Water 17 Second bath:
Water 1000 Acetic acid 10 Formaldehyde 10 Second bath (making the textiles water-repellent):
Water 1000 Aluminum acetate 30 Formaldehyde 10 Example N 0. 8 First bath: n
Paran emulsion (concentrated) 45 Nitro-cellulose alkaline solution 30 Sodium silicate 5 Gelatin 1 Sodium benzoate 2 Water 17 Second bath:
Water 1000 Acetic acid 10 Formaldehyde 10 Second bath (making the textiles water-repellent):
Water 1000 Aluminum acetate 30 Formaldehyde 10 Example No. 9 First bath:
Parain emulsion (concentrated) 45 Latex (rubber) emulsion 30 Sodium silicate 5 Gelatin 1 Sodium benannte 2 Water 17 Second bath (making the textiles water-repellent):
i Water 1000 Aluminum acetate 30 Formaldehyde 10 Textiles, fabrics, threads, etc., treated with this twobath process have shown a remarkable improvement in their Wear resistance and rubbing coelicient. Since these treated textiles have the plastic particles disposed in the nterstices of the bers and insolubilized thereon, these particles act in the same manner as ball bearings in permitting the internal sliding of the bers. While thus de-v creasing the rubbing etect on the fibers, the insolubilization of the fibers permits constant Washings of the textiles without danger of removing the plastic particles therefrom.
While I have described several embodiments of my` invention, I wish it to be understood that I do not intend to be restricted solely thereto and that I do intend to cover all modications therein which would be apparent to one skilled in the art and which come Within the spirit and scope of my invention.
What I claim as my invention is:
1. A process of treating textile material to increase its wear resistance comprising the steps of steeping the textile material in a rst bath comprising an aqueous emulsion of an emulsiable resin, parain emulsion, and gelatin, and then steeping said treated textile in a second bath comprising formaldehyde and a member selected from the group consisting of acetic acid and aluminum acetate.
2. A process ,of treating textile material to increase its wear resistance comprising the steps of steeping the textile material in a first bath comprising an aqueous emulsion of an emulsiable resin, a plasticizing component for said resin selected from the group consisting of parain, petroleum jelly, and wax, gelatin, and a member selected from the group `consisting of sodium borate and sodium silicate; and then steeping said treated textile in a second bath consisting of water, formaldehyde, and a member selected from the group consisting of acetic acid and aluminum acetate.
References Cited in the file-of this patent UNITED STATES PATENTS 690,868 Menzies Ian. 7, 1902 1,476,562 Wright Dec. 4, 1923 2,186,750 Carter lan. 9, 1940 2,354,662 Bryce Aug. 1, 1944 2,357,917 Stull Sept. 12, 1944 2,368,948 Stallings Feb. 6, 1945 2,495,845 Jefferson Ian. 31, 1950 2,790,736 McLaughlin Apr. 30, 1957
Claims (1)
1. A PROCESS OF TREATING TEXTILE MATERIAL TO INCREASE ITS WEAR RESISTANCE COMPRISING THE STEPS OF STEEPING THE TEXTILE MATERIAL IN A FIRST BATH COMPRISING AN AQUEOUS EMULSION OF AN EMULSIFIABLE RESIN, PARAFIN EMULSION, AND GELATIN, AND THEN STEEPING SAID TREATED TEXTILE IN A SECOND BATH COMPRISING FORMALSEHYDE AND A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACETIC ACID ALUMINUM ACETATE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US431603A US2871145A (en) | 1954-05-21 | 1954-05-21 | Process of impregnating textile material to increase its wear resistance |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US431603A US2871145A (en) | 1954-05-21 | 1954-05-21 | Process of impregnating textile material to increase its wear resistance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2871145A true US2871145A (en) | 1959-01-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US431603A Expired - Lifetime US2871145A (en) | 1954-05-21 | 1954-05-21 | Process of impregnating textile material to increase its wear resistance |
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| Country | Link |
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| US (1) | US2871145A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3162633A (en) * | 1958-12-24 | 1964-12-22 | American Cyanamid Co | Perfluoroguanamines |
| US3167446A (en) * | 1961-03-08 | 1965-01-26 | Lederfabriek L Mombers Nv | Coated textile materials and process |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US690868A (en) * | 1901-07-08 | 1902-01-07 | James Menzies | Process of waterproofing fabrics. |
| US1476562A (en) * | 1920-05-22 | 1923-12-04 | Wilbur L Wright | Rendering paper material and the like grease and water proof |
| US2186750A (en) * | 1935-12-03 | 1940-01-09 | Nat Processes Ltd | Rotproofing and waterproofing of materials |
| US2354662A (en) * | 1941-07-16 | 1944-08-01 | Eastman Kodak Co | Method of sizing paper |
| US2357917A (en) * | 1940-06-13 | 1944-09-12 | Nat Oil Prod Co | Resin emulsions |
| US2368948A (en) * | 1941-04-24 | 1945-02-06 | Rohm & Haas | Process for increasing the transparency of fabrics containing filament yarns |
| US2495845A (en) * | 1946-12-17 | 1950-01-31 | Atlas Powder Co | Textile sizing composition |
| US2790736A (en) * | 1955-01-31 | 1957-04-30 | Rohm & Haas | Methods of making coated paper products and the products obtained |
-
1954
- 1954-05-21 US US431603A patent/US2871145A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US690868A (en) * | 1901-07-08 | 1902-01-07 | James Menzies | Process of waterproofing fabrics. |
| US1476562A (en) * | 1920-05-22 | 1923-12-04 | Wilbur L Wright | Rendering paper material and the like grease and water proof |
| US2186750A (en) * | 1935-12-03 | 1940-01-09 | Nat Processes Ltd | Rotproofing and waterproofing of materials |
| US2357917A (en) * | 1940-06-13 | 1944-09-12 | Nat Oil Prod Co | Resin emulsions |
| US2368948A (en) * | 1941-04-24 | 1945-02-06 | Rohm & Haas | Process for increasing the transparency of fabrics containing filament yarns |
| US2354662A (en) * | 1941-07-16 | 1944-08-01 | Eastman Kodak Co | Method of sizing paper |
| US2495845A (en) * | 1946-12-17 | 1950-01-31 | Atlas Powder Co | Textile sizing composition |
| US2790736A (en) * | 1955-01-31 | 1957-04-30 | Rohm & Haas | Methods of making coated paper products and the products obtained |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3162633A (en) * | 1958-12-24 | 1964-12-22 | American Cyanamid Co | Perfluoroguanamines |
| US3167446A (en) * | 1961-03-08 | 1965-01-26 | Lederfabriek L Mombers Nv | Coated textile materials and process |
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