US3287149A - Repulpable printed paper having water resistant coating - Google Patents

Repulpable printed paper having water resistant coating Download PDF

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Publication number
US3287149A
US3287149A US25303963A US3287149A US 3287149 A US3287149 A US 3287149A US 25303963 A US25303963 A US 25303963A US 3287149 A US3287149 A US 3287149A
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Prior art keywords
repulpable
styrene
stock
coating
paper
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Expired - Lifetime
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Joseph A Dooley
Richard D Vieth
Burrell Harry
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Interchemical Corp
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Interchemical Corp
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Priority to US25303963 priority Critical patent/US3287149A/en
Priority to FR958979A priority patent/FR1379321A/en
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Publication of US3287149A publication Critical patent/US3287149A/en
Anticipated expiration legal-status Critical
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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
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/20—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C5/00—Other processes for obtaining cellulose, e.g. cooking cotton linters ; Processes characterised by the choice of cellulose-containing starting materials
    • D21C5/02—Working-up waste paper
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/64—Paper recycling
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
    • Y10T428/24851—Intermediate layer is discontinuous or differential
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
    • Y10T428/24934—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including paper layer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers

Definitions

  • Coated paper used for magazine covers must have the following properties: (1) it must have very high gloss (2) it must be resistant to water since it is generally exposed to weathering (3) it must cure rapidly since in conventional high speed coating operations for magazine covers, the curing time may be as low as a fraction of a second and (4) finally, and most important, the coated stock must be repulpable, that is the coating must be readily removable from the paper by the application of a dilute, about 2%, aqueous sodium hydroxide solution which is used in commercial deinking processes.
  • thermoset alkyd-amine coated papers have been found to be virtually unrepulpable because the coating can not be separated from the paper and the inks by a dilute alkaline solution.
  • alkyd-amine coatings do not dry at a sufliciently rapid rate to be utilizable in the high speed printing of magazine covers.
  • oleoresinous coatings have been too slow in drying when applied in the film thicknesses required for high gloss in coatings for magazine stock.
  • nitrocellulose lacquer coatings have less than desirable flammability properties and are too low in gloss for use as magazine coatings.
  • the coated paper of this invention comprises a printed magazine stock substrate coated with a copolymer comprising the copolymerization product of styrene and the half-ester formed by the half-esterification of an alphabeta unsaturated dicarboxylic acid such as fumaric or maleic acids with a lower alkanol which has 1 to 8 carbons and preferably 1 to 4 carbons, most preferably a n-alkanol such as methanol, n-propanol and n-butano'l as well as n-octanol and 2-ethyl hexanol. That this composition may be removed from the paper by treating with a dilute aqueous sodium hydroxide solution is indeed surprising because compounds containing substantial amounts of styrene are conventionally believed to have at least some alkali resistance.
  • the half-ester is first formed by esterifying the alkanol with the alpha-beta unsaturated acid, preferably at a temperature in the ragne of from 170 to 300 F., after which the half-ester is polymerized, using a conventional addition "ice polymerization catalyst, with styrene.
  • a conventional addition "ice polymerization catalyst with styrene.
  • the half-ester from about 1.1 to 5.0 moles of alkanol are preferably added for each mole of alpha-beta unsaturated acid.
  • the copolymerization preferably about from 0.5 to 2.2 moles and most preferably 1 mole of styrene are added for each mole of alpha-beta acid originally present.
  • the copolymerization is preferably conducted at a temperature of from 200 to 350 F.
  • the coatings on the paper of this invention may be readily removed during conventional repulping or deinking in which the paper is treated with about a 2% solution of sodium hydroxide.
  • EXAMPLE 2 copolymer of styrene and methyl-maleic half ester Grams Methanol Maleic anhydride 392 Xylene 624 Benzoyl peroxide 25
  • the above mixture is heated to 210 F.
  • 460 g. of propanol are added and 832 g. of styrene are added slowly over a period of one hour while the mixture is maintained at 210 F.
  • EXAMPLE 3 Copolymer of styrene and propyl-maleic half ester Grams Propanol 1480 Maleic anhydride 558 Benzoyl peroxide 30 The above mixture is heated to 210 F. Then 1248 g. styrene are added slowly over a period of one hour while the mixture is maintained at 210 F.
  • EXAMPLE 4 Copolymer of styrene and Z-ethyl hexyl-maleic half ester Grams Z-ethyl hexanol 2830 Maleic anhydride 558 Benzoyl peroxide 30 The above mixture is heated to 210 F. Then 1248 g. of styrene are added slowly over a period of one hour while the mixture is maintained at 210 F.
  • EXAMPLE 5 about 100 square inches of the stock are shredded and placed in a conventional bath for repulping magazine stock comprising 250 ml. of a 2% aqueous sodium hydroxide solution, to which there has been added 1 g. of 325 mesh mica as a filtering aid and 3 g. of a wetting agent such as the commercial Vel, sodium dodecylbenzene sulfonate, the bath having a temperature of 140 F.
  • the mixture is stirred vigorously for 15 minutes.
  • the slurry is poured onto a 40 mesh screen and washed with cold tap Water.
  • the mixture is reslurried, stirred for several minutes and again washed through a screen as described above.
  • the slurry is then vacuum dried. Careful inspection of the remaining pulp reveals that the coating has completely disintegrated and been removed.
  • EXAMPLE 6 66.7 parts of the copolymer of Example 2 are mixed with 16.7 parts of xylene and 16.6 parts of propanol and the resulting solution is coated by gravu're coating onto a magazine cover stock at 6 to 8 milligrams per square ,inch and cured in an oven at 275 F. for 10 minutes.
  • the coated stock has slightly better block resistance as well as slightly less gloss than the stock of Example 4.
  • the water resistance of the stock is excellent.
  • the remaining pulp has substantially no coating adhering to the printed or unprinted surfaces indicating that the coat-ing has been completely disintegrated.
  • EXAMPLE 7 Example is repeated using the same conditions, proportions and ingredients except that 68.9 parts of the copolymer of Example 3 are used.
  • the resulting coated stock has a block resistance slightly better than that of Example 5 but not quite as good as that of Example 6 and a gloss slightly better than that of Example 6 but not quite as good as that of Example 5.
  • the water resistance of the stock is excellent.
  • Example 5 is repeated using the same conditions, proportions, and ingredients except 68.9 parts of the copolymer of Example 4 are used.
  • the resulting coated stock has about the same properties as the stock of Example 5.
  • the remaining pulp has substantially no coating adhering thereto indicating that the coating has been completely disintegrated.
  • the magazine stock described 4 in Examples 5 to 8 which is coated may and in commercial practice does contain printed matter.
  • the magazine stock may be printed upon with any conventional ink used in magazine covers e.g., heat-set inks such as inks having limed and zincated rosin binders and phenolic binders modified with a phenol formaldehyde condensate. All of these conventional inks are readily removedduring the repulping process by the action of the dilute alkali. Repulping is also known as deinking.
  • a repulpable coated paper comprising a paper substrate having printing thereon and a water resistant coating over the printing, said coating consisting essentially of the copolymerization product of styrene and the halfester formed by the half esterification of 1 mole of an alpha-beta unsaturated dicarboxylic acid selected from the group consisting of maleic and fuman'c acids with from 1.1 to 5.0 moles of a lower. alkanol, from 0.5 to 2.2

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paper (AREA)

Description

United States Patent 3,287,149 REPULPABLE PRINTED PAPER HAVING WATER RESISTANT COATING Joseph A. Dooley, Belleville, Richard D. Vieth, Kinnelon, and Harry Burrell, North Caldwell, N.J., assignors to Interchemical Corporation, New York, N.Y., a corporation of Ohio No Drawing. Filed Jan. 22, .1963, Ser. No. 253,039 6 Claims. (Cl. 117-15) The present invention relates to repulpable coated paper and more particularly to repulpable coated printed paper stock which has suflicient gloss and resistance to water or weathering to be used for magazine covers.
Coated paper used for magazine covers must have the following properties: (1) it must have very high gloss (2) it must be resistant to water since it is generally exposed to weathering (3) it must cure rapidly since in conventional high speed coating operations for magazine covers, the curing time may be as low as a fraction of a second and (4) finally, and most important, the coated stock must be repulpable, that is the coating must be readily removable from the paper by the application of a dilute, about 2%, aqueous sodium hydroxide solution which is used in commercial deinking processes.
As far as it is known to us, no previous coated paper has achieved this unique combination of properties without any attendant properties which are detrimental to the use of the coated paper as a magazine cover. It is indeed rare to find a coated paper which is highly water resistant so that it may withstand the efiects of weathering in exposed newsstands, thereby protecting printed matter, and yet may have its coating readily and completely removable by a dilute alkaline solution.
Among coated papers which have been previously tried for magazine covers, thermoset alkyd-amine coated papers have been found to be virtually unrepulpable because the coating can not be separated from the paper and the inks by a dilute alkaline solution. In addition alkyd-amine coatings do not dry at a sufliciently rapid rate to be utilizable in the high speed printing of magazine covers. On the other hand, oleoresinous coatings have been too slow in drying when applied in the film thicknesses required for high gloss in coatings for magazine stock. Furthermore, nitrocellulose lacquer coatings have less than desirable flammability properties and are too low in gloss for use as magazine coatings.
We have now found a novel coated paper which has all of the desirable required properties set forth above for magazine covers without any attendant detrimental properties.
The coated paper of this invention comprises a printed magazine stock substrate coated with a copolymer comprising the copolymerization product of styrene and the half-ester formed by the half-esterification of an alphabeta unsaturated dicarboxylic acid such as fumaric or maleic acids with a lower alkanol which has 1 to 8 carbons and preferably 1 to 4 carbons, most preferably a n-alkanol such as methanol, n-propanol and n-butano'l as well as n-octanol and 2-ethyl hexanol. That this composition may be removed from the paper by treating with a dilute aqueous sodium hydroxide solution is indeed surprising because compounds containing substantial amounts of styrene are conventionally believed to have at least some alkali resistance.
In the present specification and claims, all proportions are by weight unless otherwise stated.
In preparing the copolymers used in the coating the half-ester is first formed by esterifying the alkanol with the alpha-beta unsaturated acid, preferably at a temperature in the ragne of from 170 to 300 F., after which the half-ester is polymerized, using a conventional addition "ice polymerization catalyst, with styrene. During the formation of the half-ester from about 1.1 to 5.0 moles of alkanol are preferably added for each mole of alpha-beta unsaturated acid. During the copolymerization, preferably about from 0.5 to 2.2 moles and most preferably 1 mole of styrene are added for each mole of alpha-beta acid originally present. The copolymerization is preferably conducted at a temperature of from 200 to 350 F.
As will be illustrated in the examples, the coatings on the paper of this invention may be readily removed during conventional repulping or deinking in which the paper is treated with about a 2% solution of sodium hydroxide.
The following examples will illustrate the practice of this invention.
EXAMPLE 1 Copolymer of styrene and butyl-maleic half ester Grams Butanol 1836 Maleic anhydride 558 Benzoyl peroxide 30 The above mixture is heated to 210 F. Then 1248 g. of styrene are added slowly over a period of 1 hour while the mixture is maintained at said temperature. Heating is continued until a viscosity of about Z on the Gardner- Holdt Scale is achieved.
EXAMPLE 2 copolymer of styrene and methyl-maleic half ester Grams Methanol Maleic anhydride 392 Xylene 624 Benzoyl peroxide 25 The above mixture is heated to 210 F. Then 460 g. of propanol are added and 832 g. of styrene are added slowly over a period of one hour while the mixture is maintained at 210 F.
EXAMPLE 3 Copolymer of styrene and propyl-maleic half ester Grams Propanol 1480 Maleic anhydride 558 Benzoyl peroxide 30 The above mixture is heated to 210 F. Then 1248 g. styrene are added slowly over a period of one hour while the mixture is maintained at 210 F EXAMPLE 4 Copolymer of styrene and Z-ethyl hexyl-maleic half ester Grams Z-ethyl hexanol 2830 Maleic anhydride 558 Benzoyl peroxide 30 The above mixture is heated to 210 F. Then 1248 g. of styrene are added slowly over a period of one hour while the mixture is maintained at 210 F.
EXAMPLE 5 about 100 square inches of the stock are shredded and placed in a conventional bath for repulping magazine stock comprising 250 ml. of a 2% aqueous sodium hydroxide solution, to which there has been added 1 g. of 325 mesh mica as a filtering aid and 3 g. of a wetting agent such as the commercial Vel, sodium dodecylbenzene sulfonate, the bath having a temperature of 140 F. The mixture is stirred vigorously for 15 minutes. The slurry is poured onto a 40 mesh screen and washed with cold tap Water. The mixture is reslurried, stirred for several minutes and again washed through a screen as described above. The slurry is then vacuum dried. Careful inspection of the remaining pulp reveals that the coating has completely disintegrated and been removed.
EXAMPLE 6 66.7 parts of the copolymer of Example 2 are mixed with 16.7 parts of xylene and 16.6 parts of propanol and the resulting solution is coated by gravu're coating onto a magazine cover stock at 6 to 8 milligrams per square ,inch and cured in an oven at 275 F. for 10 minutes. The coated stock has slightly better block resistance as well as slightly less gloss than the stock of Example 4. The water resistance of the stock is excellent. When tested for repulpability in accordance with the procedure of Example 4, the remaining pulp has substantially no coating adhering to the printed or unprinted surfaces indicating that the coat-ing has been completely disintegrated.
EXAMPLE 7 Example is repeated using the same conditions, proportions and ingredients except that 68.9 parts of the copolymer of Example 3 are used. The resulting coated stock has a block resistance slightly better than that of Example 5 but not quite as good as that of Example 6 and a gloss slightly better than that of Example 6 but not quite as good as that of Example 5. The water resistance of the stock is excellent.
When tested for repulpability in accordance with the procedure of Example 5, the remaining pulp has substantially no coating adhering thereto indicating that the coating has been completely disintegrated.
EXAMPLE 8 Example 5 is repeated using the same conditions, proportions, and ingredients except 68.9 parts of the copolymer of Example 4 are used. The resulting coated stock has about the same properties as the stock of Example 5. When tested for repulpability in accordance with the procedure of Example 5, the remaining pulp has substantially no coating adhering thereto indicating that the coating has been completely disintegrated.
It should be noted that the magazine stock described 4 in Examples 5 to 8 which is coated may and in commercial practice does contain printed matter. The magazine stock may be printed upon with any conventional ink used in magazine covers e.g., heat-set inks such as inks having limed and zincated rosin binders and phenolic binders modified with a phenol formaldehyde condensate. All of these conventional inks are readily removedduring the repulping process by the action of the dilute alkali. Repulping is also known as deinking.
While :there have been described what is at present considered to be the preferred embodiments of this invention, it will be obvious to those skilled in the art that various changes and modifications may be made therein.
without departing from the invention, and it is, therefore, aimed to cover all such changes and modifications as fall within the true spirit and scope of the invention.
What is claimed is: 1. A repulpable coated papercomprising a paper substrate having printing thereon and a water resistant coating over the printing, said coating consisting essentially of the copolymerization product of styrene and the halfester formed by the half esterification of 1 mole of an alpha-beta unsaturated dicarboxylic acid selected from the group consisting of maleic and fuman'c acids with from 1.1 to 5.0 moles of a lower. alkanol, from 0.5 to 2.2
moles of styrene being copolymerized for each mole of said acid.
2. The repulpable coated paper of claim 1 wherein said alkanol has from 1 to 4 carbons.
3. The repulpable coated paper of claim 1 wherein said half-ester is the methyl half-ester of maleic .acid.
4. The repulpable coated paper of claim 1 wherein said half-ester is the propyl half-ester of maleic acid.
5. The repulpable coated paper of claim 1 wherein said half-ester is the butyl half-ester of maleic acid.
6. The repulpable coated paper of claim 1 wherein said half-ester is the 2-ethyl hexyl half-ester of maleic acid.
WILLIAM D. MARTIN, Primary Examiner.
MORRIS O. WOLK, S. L. BASHORE, H. W. MYLIUS.
Assistant Examiners.
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No 3, 287 ,149 November 22 1966 Joseph A. Dooley et a1.
It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Column 1, line 71, for "ragne" read range column 2, line 8, for "350 F." read 250 F.
Signed and sealed this 12th day of September 1967.
( AL) Attest:
ERNEST W. SWIDER EDWARD]. BRENNER Attesting Officer Commissioner of Patents

Claims (1)

1. A REPULPABLE COATED PAPER COMPRISING A PAPER SUBSTRATE HAVING PRINTING THEREON AND A WATER RESISTANT COATING OVER THE PRINTING, SAID COATING CONSISTING ESSENTIALLY OF THE COPOLYMERIZATION PRODUCT OF STYRENE AND THE HALFESTER FORMED BY THE HALF ESTERIFICATION OF 1 MOLE OF AN ALPHA-BETA UNSATURATED DICARBOXYLIC ACID SELECTED FROM THE GROUP CONSISTING OF MALEIC AND FUMARIC ACIDS WITH FROM 1.1 TO 5.0 MOLES OF A LOWER ALKANOL, FROM 0.5 TO 2.2 MOLES OF STYRENE BEING COPOLYMERIZED FOR EACH MOLE OF SAID ACID.
US25303963 1963-01-22 1963-01-22 Repulpable printed paper having water resistant coating Expired - Lifetime US3287149A (en)

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FR958979A FR1379321A (en) 1963-01-22 1963-12-31 New coated paper convertible to pulp

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5133833A (en) * 1991-02-26 1992-07-28 Kimberly-Clark Corporation Process for repulping of fiber-latex binder composites
US5491190A (en) * 1993-07-22 1996-02-13 S. C. Johnson & Son, Inc. Repulpable hot melt polymer/fatty acid compositions for fibrous products
DE4441302A1 (en) * 1994-11-21 1996-05-23 Leuna Werke Gmbh Process for the production of a size precursor
US5700516A (en) * 1993-07-22 1997-12-23 S. C. Johnson Commerical Markets, Inc. Repulpable hot melt polymer/wax compositions for fibrous products
US5885738A (en) * 1995-01-17 1999-03-23 W. L. Gore & Associates, Inc. Method for making and using an improved durable printable sheet
US5990377A (en) * 1997-03-21 1999-11-23 Kimberly-Clark Worldwide, Inc. Dual-zoned absorbent webs
US6113738A (en) * 1998-03-16 2000-09-05 Nalco Chemical Company Use of additives to breakdown and stabilize wax during fiber recycle
US6395957B1 (en) 1997-03-21 2002-05-28 Kimberly-Clark Worldwide, Inc. Dual-zoned absorbent webs
US6548558B2 (en) 1998-03-16 2003-04-15 Ondeo Nalco Company Contaminant dispersants useful in recycling of treated containers

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1870358A (en) * 1930-12-02 1932-08-09 Kellogg Dils Inc Process of treating printed paper for use as paper making stock
US1966238A (en) * 1933-04-19 1934-07-10 Hinde & Dauch Paper Co Paper for corrugating pueposes and process of forming the same
US2047398A (en) * 1930-06-26 1936-07-14 Ig Farbenindustrie Ag Artificial resins and process of making them
US2254382A (en) * 1938-10-03 1941-09-02 Rohm & Haas Polymerizable mono-esters of maleic acid and polymers derived therefrom
US2320724A (en) * 1940-03-14 1943-06-01 Pittsburgh Plate Glass Co Method of treating styrene-unsaturated dicarboxylic acid resins
US2576914A (en) * 1948-02-28 1951-12-04 Monsanto Chemicals Coated papers and methods and compositions for preparing same
US2667462A (en) * 1950-10-24 1954-01-26 Monsanto Chemicals Adhesive from monoethylenically unsaturated dicarboxylic acid salt polymer
US3002860A (en) * 1959-04-16 1961-10-03 Monsanto Chemicals Paper sized with nitreous salt of maleic anhydride - styrene copolymer and epoxy resin mixture
US3020178A (en) * 1957-09-06 1962-02-06 Rohm & Haas Paper impregnating compositions, impregnated papers and the process of impregnating paper

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2047398A (en) * 1930-06-26 1936-07-14 Ig Farbenindustrie Ag Artificial resins and process of making them
US1870358A (en) * 1930-12-02 1932-08-09 Kellogg Dils Inc Process of treating printed paper for use as paper making stock
US1966238A (en) * 1933-04-19 1934-07-10 Hinde & Dauch Paper Co Paper for corrugating pueposes and process of forming the same
US2254382A (en) * 1938-10-03 1941-09-02 Rohm & Haas Polymerizable mono-esters of maleic acid and polymers derived therefrom
US2320724A (en) * 1940-03-14 1943-06-01 Pittsburgh Plate Glass Co Method of treating styrene-unsaturated dicarboxylic acid resins
US2576914A (en) * 1948-02-28 1951-12-04 Monsanto Chemicals Coated papers and methods and compositions for preparing same
US2667462A (en) * 1950-10-24 1954-01-26 Monsanto Chemicals Adhesive from monoethylenically unsaturated dicarboxylic acid salt polymer
US3020178A (en) * 1957-09-06 1962-02-06 Rohm & Haas Paper impregnating compositions, impregnated papers and the process of impregnating paper
US3002860A (en) * 1959-04-16 1961-10-03 Monsanto Chemicals Paper sized with nitreous salt of maleic anhydride - styrene copolymer and epoxy resin mixture

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5133833A (en) * 1991-02-26 1992-07-28 Kimberly-Clark Corporation Process for repulping of fiber-latex binder composites
US5491190A (en) * 1993-07-22 1996-02-13 S. C. Johnson & Son, Inc. Repulpable hot melt polymer/fatty acid compositions for fibrous products
US5587202A (en) * 1993-07-22 1996-12-24 S. C. Johnson & Son, Inc. Repulpable hot melt polymer/fatty acid compositions for fibrous products
US5599596A (en) * 1993-07-22 1997-02-04 S. C. Johnson & Son, Inc. Repulpable hot melt polymer/fatty acid compositions for fibrous products
US5700516A (en) * 1993-07-22 1997-12-23 S. C. Johnson Commerical Markets, Inc. Repulpable hot melt polymer/wax compositions for fibrous products
DE4441302A1 (en) * 1994-11-21 1996-05-23 Leuna Werke Gmbh Process for the production of a size precursor
US5885738A (en) * 1995-01-17 1999-03-23 W. L. Gore & Associates, Inc. Method for making and using an improved durable printable sheet
US5990377A (en) * 1997-03-21 1999-11-23 Kimberly-Clark Worldwide, Inc. Dual-zoned absorbent webs
US6395957B1 (en) 1997-03-21 2002-05-28 Kimberly-Clark Worldwide, Inc. Dual-zoned absorbent webs
US6911573B2 (en) 1997-03-21 2005-06-28 Kimberly-Clark Worldwide, Inc. Dual-zoned absorbent webs
US6113738A (en) * 1998-03-16 2000-09-05 Nalco Chemical Company Use of additives to breakdown and stabilize wax during fiber recycle
US6248793B1 (en) 1998-03-16 2001-06-19 Nalco Chemical Company Contaminant dispersants useful in recycling of treated containers
US6548558B2 (en) 1998-03-16 2003-04-15 Ondeo Nalco Company Contaminant dispersants useful in recycling of treated containers

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