US2666713A - Plasticizer and moisture retentive composition for paper and paper containing it - Google Patents
Plasticizer and moisture retentive composition for paper and paper containing it Download PDFInfo
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- US2666713A US2666713A US143166A US14316650A US2666713A US 2666713 A US2666713 A US 2666713A US 143166 A US143166 A US 143166A US 14316650 A US14316650 A US 14316650A US 2666713 A US2666713 A US 2666713A
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- paper
- sugar
- composition
- moisture
- urea
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- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 27
- 239000004014 plasticizer Substances 0.000 title claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 31
- 239000004202 carbamide Substances 0.000 claims description 17
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 11
- 150000001241 acetals Chemical class 0.000 claims description 11
- 239000000470 constituent Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 description 19
- 239000000123 paper Substances 0.000 description 18
- -1 cyclic acetal Chemical class 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229930182470 glycoside Natural products 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 8
- 150000002338 glycosides Chemical class 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000008121 dextrose Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229930182479 fructoside Natural products 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011086 glassine Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 2
- 229960003868 paraldehyde Drugs 0.000 description 2
- 229940044654 phenolsulfonic acid Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- 101100505161 Caenorhabditis elegans mel-32 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
- D21H17/24—Polysaccharides
Definitions
- 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.
- 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.
- 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,-
- 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-
- 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 coside such 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.
- 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.
- a suitable sugar such as dextrose or invert sugar
- an aldehyde, ketone or alcohol of not more than three carbon atoms in the presence of a suitable acid catalyst.
- the acetal or glucoside may be present in the final solution in amounts between 1 and Examples of the manner of making the com-.
- 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.
- 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..
- DB mixed sugar such as dextrose
- tatli'e desired solutions and concentration.
- composition as claimed in claim 1 wherein the alkylidene group has three carbon atoms.
- composition as claimed in claim 1 wherein the cyclic acetal of a sugar is monoisonmnylidene glucose.
- compositions for paper 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.
- acetal of the glycoside is monoisopropylidene ethyl fructoside.
- 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".
- 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?
Landscapes
- Paper (AREA)
Description
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.
Examplesag.
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..,usedv.in. 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.
LOUIS LANG; RONALD J. BAIRD.
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.
Claims (1)
1. A PLASTICIZER AND MOISTURE RETENTIVE COMPOSITION FOR PAPER, THE ESSENTIAL PAPER 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 AND ONE OF UREA TO NINE OF THE SUGAR, AND (III) A WATER-SOLUBLE CYCLIC ACETAL OF A SUGAR IN AN AMOUNT FROM ONE OF FIFTY PERCENT BY WEIGHT OF THE COMPOSITION AND WITH UNDER FOUR CARBON ATOMS IN THE ALKYLIDENE GROUP.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US143166A US2666713A (en) | 1950-02-08 | 1950-02-08 | Plasticizer and moisture retentive composition for paper and paper containing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US143166A US2666713A (en) | 1950-02-08 | 1950-02-08 | Plasticizer and moisture retentive composition for paper and paper containing it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2666713A true US2666713A (en) | 1954-01-19 |
Family
ID=22502878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US143166A Expired - Lifetime US2666713A (en) | 1950-02-08 | 1950-02-08 | Plasticizer and moisture retentive composition for paper and paper containing it |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2666713A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956963A (en) * | 1954-08-02 | 1960-10-18 | Nat Sugar Refining Company | Saccharide-monohydroxy aldehyde reaction product and method of preparing same |
| US3043720A (en) * | 1957-05-28 | 1962-07-10 | Dow Chemical Co | Cellulosic materials plasticized with hydroxypropylsucrose |
| WO1998016687A1 (en) * | 1996-10-11 | 1998-04-23 | Eastman Chemical Company | Composition and paper comprising cellulose ester and alkylpolyglycosides |
| US6193841B1 (en) | 1998-11-30 | 2001-02-27 | Eastman Chemical Company | Shaped, plastic articles comprising a cellulose fiber, a cellulose ester, and a non-ionic surfactant |
| US20060151988A1 (en) * | 2005-01-13 | 2006-07-13 | Shinyo Engineering Limited | Paper ring, printed material or calendar using such ring, and method for manufacture thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US148319A (en) * | 1874-03-10 | Improvement in sizing cloths | ||
| US2000807A (en) * | 1933-07-07 | 1935-05-07 | Kelco Co | Readily water soluble dry alginate |
| US2025044A (en) * | 1931-11-05 | 1935-12-24 | Dreyfus Henry | Application of new organic ethers |
| GB467749A (en) * | 1935-02-27 | 1937-06-23 | Theodor Rotta | Manufacture of urea compounds useful for the treatment of textiles |
| US2326118A (en) * | 1940-10-04 | 1943-08-10 | Stein Hall Mfg Co | Pregummed hanging material |
-
1950
- 1950-02-08 US US143166A patent/US2666713A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US148319A (en) * | 1874-03-10 | Improvement in sizing cloths | ||
| US2025044A (en) * | 1931-11-05 | 1935-12-24 | Dreyfus Henry | Application of new organic ethers |
| US2000807A (en) * | 1933-07-07 | 1935-05-07 | Kelco Co | Readily water soluble dry alginate |
| GB467749A (en) * | 1935-02-27 | 1937-06-23 | Theodor Rotta | Manufacture of urea compounds useful for the treatment of textiles |
| US2116640A (en) * | 1935-02-27 | 1938-05-10 | Chem Fab Theod | Production of molecular compounds |
| US2326118A (en) * | 1940-10-04 | 1943-08-10 | Stein Hall Mfg Co | Pregummed hanging material |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956963A (en) * | 1954-08-02 | 1960-10-18 | Nat Sugar Refining Company | Saccharide-monohydroxy aldehyde reaction product and method of preparing same |
| US3043720A (en) * | 1957-05-28 | 1962-07-10 | Dow Chemical Co | Cellulosic materials plasticized with hydroxypropylsucrose |
| WO1998016687A1 (en) * | 1996-10-11 | 1998-04-23 | Eastman Chemical Company | Composition and paper comprising cellulose ester and alkylpolyglycosides |
| US6228895B1 (en) | 1996-10-11 | 2001-05-08 | Eastman Chemical Company | Method for plasticizing a composition comprised of cellulose fiber and a cellulose ester |
| US6268028B1 (en) | 1996-10-11 | 2001-07-31 | Eastman Chemical Company | Composition and paper comprising cellulose ester, alkylpolyglycosides, and cellulose |
| US6309509B1 (en) | 1996-10-11 | 2001-10-30 | Eastman Chemical Company | Composition and paper comprising cellulose ester, alkylpolyglycosides, and cellulose |
| US6193841B1 (en) | 1998-11-30 | 2001-02-27 | Eastman Chemical Company | Shaped, plastic articles comprising a cellulose fiber, a cellulose ester, and a non-ionic surfactant |
| US20060151988A1 (en) * | 2005-01-13 | 2006-07-13 | Shinyo Engineering Limited | Paper ring, printed material or calendar using such ring, and method for manufacture thereof |
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