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Publication numberUS2666713 A
Publication typeGrant
Publication dateJan 19, 1954
Filing dateFeb 8, 1950
Priority dateFeb 8, 1950
Publication numberUS 2666713 A, US 2666713A, US-A-2666713, US2666713 A, US2666713A
InventorsBaird Ronald J, Louis Lang
Original AssigneeNat Sugar Refining Company
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Plasticizer and moisture retentive composition for paper and paper containing it
US 2666713 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

Patented Jan. 19, 1954 UNITED ,STATES PATENT orncr.

PLASTICIZER AND MOISTURE RETENTIVE COD/[POSITION FOR PAPER AND PAPER CONTAINING IT Louis Lang and Ronald J. Baird, Philadelphia, Pa,- assignors to The National Sugar Refining Company,'New York, N. Y., a corporation of New Jersey N Drawing. Application February 8, 1950,

' Serial No. 43,16

- Our invention relates to a composition applicable to paper in the process of making same to plasticize the paper and make it suificiently moisture retentive to prevent its drying to brittleness and to the paper so prepared.

Heretofore glycerine or' compositions contaming glycerine have been used in the making of paper to enable the paper to retain moisture to a sufficient extent to render it pliable and flexible, a small amount of the glycerinawhich has a tendency to absorb and hold moisture," being retained in the finished paper. A

Our present invention relates to a composition having excellent water retentive properties, which may be made cheaply and without limita tion as to the quantity available and which,-

therefore, serves asan excellent lubricant and moisture retaining agent for paper.

The compositionof our invention comprises an admixture, preferably as a concentrated solution, of a suganurea', and a glycoside, or a cyclic acetal of a sugar'or glycoside. The glycoside may be, for example, an alkyl glycoside such as methylglycoside, ethyl fructoside, etc., and the acetal may be monoisopropylidene glucose, di-

16 Claims. (01. 106-162) 2 Y Examples of the aldehydes, ketones and alcohols suitable for this purpose are: formaldehyde; paraformaldehyde (polyoxymethylene); trioxane; acetaldehyde; paraldehyde; acetone; methanol; ethanol; isopropanol and normal propyl alcohol. Any combination of the above may be used as well as any'individual of the above group. Y

The acid catalyst maybe, for example, phenols'ulfonic acid or ,toluo'sulfonic acid or sulfuric acid. The acetal produced from any of ;;the above materials is a water soluble compound and maybe dissolved with urea and. the sugar to produce the compositionof our invention.

The relative'proporti'ons of the urea to dextrose T or other sugar may be in the ratio of anywhere ethylidene fructose, etc. ,A mixed acetal gly- 1 cosidesuch as, for example, a cyclic acetal of an alkyl glycoside such as monoisopropylidene ethyl fructoside may be used, and mixtures of acetals and glycosides may also be used. The aldehydes and ketones from which the acetals are derived, andthe alcohols from which the glycosides are derived, have not more than three carbon atoms.

Such acetals are soluble in water and form with the sugar and urea a composition or mixture which may be taken up in .very small amount by the paper pulp in the manufacture of paper and be retained on the fibers. The quantity thus retained will be suflicient to prevent loss of all moisture by the paper without being sufiicient to render the paper too, absorptive of moisture.

under normal atmospheric conditions. 6 1 The composition maybe used to advantage with all types of paper, but more particularly with glassine paper to render the latter grease resistant and sufiicientlymoisture retentive.

' The acetals or glycosides may be formed respectively by reacting a suitable sugar, such as dextrose or invert sugar with an aldehyde, ketone or alcohol of not more than three carbon atoms in the presence of a suitable acid catalyst.

from 1 :9 to 9:1, and the acetal or glucoside may be present in the final solution in amounts between 1 and Examples of the manner of making the com-.

position are as follows: 7

Example 1 derivative.

The above compound may be admixed in aqueous solution with urea and a sugar in the proportions indicated above to form the paper plasticizer. The proportions may be adjusted to'give any degree of moisture retention and grease resistance or to suit any conditions of paper manufacture. Preferably it is made of% of solids and 25% water.

7 Example 2 210 grams of phenol sulfonic acid (mixed ortho and para isomers) are dissolved in a mixture of 14 liters acetone and 14liters ethyl alcohol S. D. A. formula #23-A). The mixture is stirred slowly with a mechanical stirrer with large paddles in a jacketed copper kettle pro- 'vided with reflux condenser, while 35 lbs. of fine granulated sugar (1. 9. sucrose) are added. Steam or hot water is then turned on in the jacket to maintain a refluxing temperature of the reacting mixture until all the sugar is dissolved (about 8 hours). The product is then stirred with a suspension of 310 grams of calcium carbonate, in i liter of Water untilthe pH is above; 6. The: product is ,filterediiandjcoriv centrated to a soft resinous consistency by evaporation of the solvents in a rapid evaporator..

The above compounds comprising mixed acetal-glucoside may then: DB mixed sugar, such as dextrose, andturea tatli'e desired: solutions and concentration.


In the equipment of ExamiqlbZi-atcreactd'zini a similar way 35 lbs. of sugar'with 14 liters of acetone, 5 liters of paraldehyde and 160 grams of phenol sulfonic acid. The-mixture -isz neittralized with 24 grams of calcium carbonate in 1 liter of water, filtered and concentraaemas ing Example 1.

Example. 4.

In a J similar way is prepared a resinous material .from 501105;. of sugar-, 8;5'=-liters of acetone,- 8i5i-lifiers ethylalcohol (95% l-.-7"li ters-of*p a-1-- aldeh yde, 1 grams ofitoluene sulfonic acid; The mixture after reaction is neutralized with powderedsodium bicarbonate-at 50 0., fl-tered'and concentrated as above.

centrated to yield 553 grams o a clear; watersoluble"resinous'material'whic I combined with urea and dextrose as in previous-examples:

Emam'ple'fia. imilar. way. re act d. 484 .1 rams. of su ar. liet'it rams cffgparaformaldehyda .1; m1. f .pamldehyde a id? 4 e' ams. of. ,tomenensulfonic acid; The' reac s2gh0urs. Tlifiiprodi. fict isneut aliz dijbx eati With? pOWdercdi'so: diurn b carbonate and'concentrateaito yield 652 rams; f a -product; which. is mixed .Witliui'fia. and dextrose ,as in; previous examples! It will be understoodthatthe abovear-e given m.e t e1y;, y w s: f. example and other. acetals, oij aldehydes and; ketones and lyt'tosidespfgalcorhols having three or less carbon atomamayeb'e similarly formedand. mixed .with, suitable..,sugars andiirea, .to form. thepaper, lubricant. .andmois: tureretentiOn, medium of, our invention.

Whereverfasugar, 01: the.. ,sugar,; is men; tioned', above,; it .is understood-that. it .is.., a generic; sense g Having, describedour invention,-what weiclaimx 1. A plasticizer and moisture retentive composition for paper, the essent-ial paper plasticizingand moisture. retentive, constituentsoi which dn i t. s e tia l .1 f; -I .asu ar arid.- (11-). urea. inj .prop'ortions.between. ,onel. of ,tnesuear to nine; of, ureaand one of urea to, nine of; the sugam and.

(HI). aiwater solublecyclic acetakv oil-a :sugardn:

4 an amount from one to fifty percent by weight of the composition and with under four carbon atoms in the alkylidene group.

2. The composition as claimed in claim 1, wherein the alkylidene group has three carbon atoms.

3. The composition as claimed in claim 1, wherein the cyclic acetal of a sugar is monoisonmnylidene glucose.

44 ,Agplasticizerhand moisture retentive composition for paper, the essential plasticizing and moisture retentive constituents of which consist essentially of (I) a sugar and (II) urea, in proportions-between one of the sugar to nine of urea a-ndlionegiof urea to nine of the sugar, and (III) a water soluble cyclic acetal of an alkyl glycoside with: under: four carbon atoms in its alkylideneqgroup and also in the alkyl group and inriamamount'zotrfrom one to fifty percent by weight oirthiecomposition.

5 The. composition as claimed in claim 4,

wherein the acetal of the glycoside is monoisopropylidene ethyl fructoside.

6t Theu composition as claimed in claim 4, wherein the sugar is dextrose.

7: A .plasticizerwandmoisture retentive; composition for; paper, fill-Q5 essentialplasticizingand moistureeretentivegconstituent ofiywhich consist essential-lypoi fl) a; sngarrand- (II), urea,- in:1pro portions betweenconezof .thezsugarsto nihezcf urea and .one of; ureantozininen ofizthezsugar; and: (III) a: waterrsoluble.=alkyluglycosidenwitln:Yunder' four carbon-atomsimits alkyl:grouprainicin aniamount of. Ffrom one. .1 to; fifty percent .bmwveig-ht of; the composition".

89 The composiifio'nz; as claimed:: claim: 7', wherein the alkyliglycosideiisimethyl:.gluccside.

92 ,.A: plasticizenand moisture retentive'i-composition for pap-er'; thevessentiala-paper: plasticizs ing -and moisture:retentiveconstituentsof which consist essentially-"ci il; a sugars-andc (11)" urea; in proportions between-one of: the sugar to -nine of urea and one oi 'ur eato:nineof-the sugarand (-III)"= at least oni'a' tvater-soluble constituent of the-class-cons isting oi? (m e/cyclic acetal of 'a sugar with under-four carbon atoms the alkyl idene 'g'roup; (bran-alarm glycoside with under four carbon amms in-tlrie-alkyl group and we) a cy clic-acetal or suc' lkyl gl 'rco'side with under four ca-rbon atom'sit'sfalkylidene grotip; the water -soluble constituenWIILamountingto-irom one to fi ftyfipercent bywei'g-ht OfthGTCOmDQSiHOIE 10; The" compositiunias---claimedin claim 9; wherein :th'efiugarjs "sucrose.

1 1'. The compOSition'; asxclaimedrin' claim? 9: whereimthesugjar is ldextrose.

12.. The -zcomppsition as. claimed'lin claim 9, whereimthe. plasticiz'ing'.,and moisture retentive constituents are, dissolved .in water...

13.; Theecomposition, ass, claimed. in claim 12, wherein: the plasticizinggande moisture (retentive constituents :areadissclved 4m concentrated. S0111. tionz'ina'watens l fIhe :compositionuaszxclaimedi 1115212331112; wherein the waterconten is twentyafivepercent;

15. A papencontaining suflicient cfia plasticizerand moistureretentive compesitiomto'prevent-loss of- 'all of its moisture andless than'the amount that would 'render';the paperitoo absorptiveof moisture under normal atmospheric conditions; and in, which. theplasticiz'er and) moisture. retentime .-.comp.osition. is, the. comp.osition...of.. claim 9.

16.x. A.',pape r .as.. c1aimed-in..c1aim .15;. wherein the paperaispglassine. and=said glassine. islgreases,

resistant because of its content of the plasticizer and moisture retentive composition.


References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 148,319 Newton Mar. 10, 1874 2,000,807 Wig May '1, 1935 2,025,044 Dreyfus Dec. 24, 1935 OTHER REFERENCES Gregory, Uses 8: Applications of Chemicals 8: Related Materials, (1939) pages 628-630 and 631.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US148319 *Feb 28, 1874Mar 10, 1874 Improvement in sizing cloths
US2000807 *Jul 7, 1933May 7, 1935Kelco CoReadily water soluble dry alginate
US2025044 *Oct 20, 1932Dec 24, 1935Dreyfus HenryApplication of new organic ethers
US2116640 *Feb 24, 1936May 10, 1938Chem Fab TheodProduction of molecular compounds
US2326118 *Oct 4, 1940Aug 10, 1943Stein Hall Mfg CoPregummed hanging material
GB467749A * Title not available
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2956963 *Aug 2, 1954Oct 18, 1960Nat Sugar Refining CompanySaccharide-monohydroxy aldehyde reaction product and method of preparing same
US3043720 *May 28, 1957Jul 10, 1962Dow Chemical CoCellulosic materials plasticized with hydroxypropylsucrose
US6193841Nov 30, 1998Feb 27, 2001Eastman Chemical CompanyShaped, plastic articles comprising a cellulose fiber, a cellulose ester, and a non-ionic surfactant
US6228895Nov 30, 1998May 8, 2001Eastman Chemical CompanyMethod for plasticizing a composition comprised of cellulose fiber and a cellulose ester
US6268028Nov 30, 1998Jul 31, 2001Eastman Chemical CompanyComposition and paper comprising cellulose ester, alkylpolyglycosides, and cellulose
US6309509Oct 11, 1996Oct 30, 2001Eastman Chemical CompanyComposition and paper comprising cellulose ester, alkylpolyglycosides, and cellulose
WO1998016687A1 *Oct 6, 1997Apr 23, 1998Eastman Chem CoComposition and paper comprising cellulose ester and alkylpolyglycosides
U.S. Classification106/217.6, 536/4.1, 536/1.11
International ClassificationD21H17/00, D21H17/24
Cooperative ClassificationD21H17/24
European ClassificationD21H17/24