US2926116A - Wet-strength paper and method of making same - Google Patents

Wet-strength paper and method of making same Download PDF

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Publication number
US2926116A
US2926116A US682086A US68208657A US2926116A US 2926116 A US2926116 A US 2926116A US 682086 A US682086 A US 682086A US 68208657 A US68208657 A US 68208657A US 2926116 A US2926116 A US 2926116A
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US
United States
Prior art keywords
paper
polyamide
resin
epichlorohydrin
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US682086A
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English (en)
Inventor
Gerald I Keim
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hercules Powder Co
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Hercules Powder Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27505392&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US2926116(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to NL231136D priority Critical patent/NL231136A/xx
Priority to NL110447D priority patent/NL110447C/xx
Priority to US447411A priority patent/US1476116A/en
Application filed by Hercules Powder Co filed Critical Hercules Powder Co
Priority to US682086A priority patent/US2926116A/en
Priority claimed from US694909A external-priority patent/US3049469A/en
Priority to GB26945/58A priority patent/GB865727A/en
Priority to DEH34226A priority patent/DE1177824B/de
Priority to DE1546369A priority patent/DE1546369C3/de
Priority to FR38672A priority patent/FR1265829A/fr
Priority to US796743A priority patent/US2926154A/en
Publication of US2926116A publication Critical patent/US2926116A/en
Application granted granted Critical
Priority to US792161*A priority patent/US3483077A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
    • D21H17/55—Polyamides; Polyaminoamides; Polyester-amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/48—Polymers modified by chemical after-treatment
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/59—Polyamides; Polyimides
    • D06M15/595—Derivatives obtained by substitution of a hydrogen atom of the carboxamide radical

Definitions

  • This invention relates to the manufacture of resintreated cellulosic fibers and fibrous products prepared therefrom and is directed particularly to a method for improving the wet strength of felted fibrous cellulosic materials such as paper, paperboard, shaped paper articles and the like.
  • the invention includes the improved cellulosic fibers and fibrous products themselves as well as methods'of preparing these products from aqueous suspensions of fibrous cellulosic material such as paper pulp.
  • a principal object of the present invention is the pro vision of-ta ".mfilhod tor adding wet-strength to -any type of paper regardless of whetherit is produced under acid, neutral or alkalinerconditions.
  • the-above and other objects are accomplished'byapplying to fibrouscellulosic material such as paper pulp an uncured thermosetting
  • the dibasic carboxylic acid is first reacted with the polyalkylene'polyamine, preferably in aqueous solution,. underconditions.suchasto produce a-watersoluble polyamide containing-the recurring groups wh'eren and x are each 2 or more and 'Ris the divalent hydrocarbon radical of the dibasic carboxylic acid.
  • This water-solublepolyamide is then reacted with epichloro hydrin to .form the water-soluble cationic therrnosetting resin.
  • the dicarboxylic acids contemplated for use in preparirigthe resins. of the invention are the saturated aliphatic dibasic carboxylic acidscontaining from 3'to 10carbon atoms such as succinic, adipic, azelaic and the like.
  • the saturated dibasicacids having from 4'to 8carbon atoms inthe molecule are preferred."
  • Blends of two or. more of the saturated 'dibasic carboxylic acids may;.also.
  • polyaltkylene polyamines including polyethylene polyamines, polypropylene polyamines, polybutYlenepo1yamines-and so "on may be employed of which It hasbeen found that resins of,
  • the polyalkylene polyamines contemplated for use may be represented as polyamines in which the nitrogen atoms are linked together by groups of the formula -C,,H where n is a small integer greater than unity and the number of such groups in themolecule ranges from two up to about eight.
  • nitrogen atoms may be attached to adjacent carbon atoms in' 'the group -C,',H or to carbon atoms further apart, but not to the same carbon atom.
  • This invention contemplates not only the use of such. polyamines as diethylenetriamine, triethylenetetramine, tetraethylenep enta mine, and dipropylenetriamine, which can be obtained in' reasonably pure form, but also mixtures and. various crude polyamine materials.
  • the tennpolyalkylene polyamine employed in the claims therefore, refers to and includes any of the polyalkylene polyamines referred to above or to a mixture of such polyalkylene polyamines.
  • polyalkylene polyamine up to about of the polyalkylene polyamine may be replaced by 'a molecularly equivalent amount of the diamine. will serve the purpose.
  • the temperatures employed for carrying out the reac tion between-the-dibasic-acid and the polyalkylene polyamine mayvary. from about C. to about 250 C. or-higher at atmospheric pressure.
  • reaction is desirably continued to substantial completion for best results.
  • anamount ofdibasic acid sufficie'nt to react substantially completelywith the primary-amine groups of the polyalltyle'ne polyamine but insufiicient to react with the sec-- ondary amine groups to any substantial extent.
  • This will.usually require a mole ratio of polyalkylene polyamine to dibasic acid of from about 0.921 to about 1.2: 1.
  • mole ratios of from about 0.8:1 to about 1.4:1
  • mole ratios below about 0.8:l result in a gelled product or one having a pronounced tendency to gel while mole ratios above 1.4:1 result in low molecular weight polyamides.
  • Suchproducts do not produce efiicient wetstrength resins when reacted with epichlorohydrin.
  • pHadjustm'ent is usual ly notnecessary However, since the pHz; decreasesduringahe polymerization: phase of the reaction
  • the mixture Usually; a replacement of about 50% or less' For most purposes; however,- temperatures-between about C. and 210" C(h'avebeen found satisfactory and are preferred. Where itmay be desirable, in some cases, to add alkali to combine with at least some of the acid formed. This will create an environment favoring the conversion of the chlorohydrin groups to epoxide groups, thereby increasing the ratio of the latter to the former.
  • sufiicient water is then added to adjust'the solids content of the resin solution to the desired amount, i.e., about 10% more or less, the product cooled to about 25 C. and then stabilized by adding suificient acid to reduce the pH at least to about 6 and preferably to about 5.
  • Any suitable acid such as hydrochloric, sulfuric, nitric, formic, phosphoric and acetic acid may be used to stabilize the product.
  • hydrochloric acid is preferred.
  • the cationic polyamide-epichlorohydrin resins may be applied to paper or other felted cellulosic products by tub application or by spraying, if desired.
  • preformed and partially or completely dried paper may be impregnated by immersion in, or spraying with, an aqueous solution of the resin following which the paper may be heated for about 0.5 to 30 minutes at temperatures of 90 C. to 100 C. or higher to dry same and cure the resin to a water-insoluble condition.
  • the resulting paper has greatly increased wet strength, and, therefore, this method is well suited for the impregnation of paper towels, absorbent tissue and the like as well as heavier stocks such as wrapping paper, bag paper and the like to impart wet strength characteristics thereto.
  • the preferred method of incorporating these resins in paper is by internal addition prior to sheet formation whereby advantage is taken of the substantivity of the resins for hydrated cellulosic fibers.
  • an aqueous solution of the resin in its uncured and hydrophilic state is added to an aqueous suspension of paper stock in the beater, stock chest,
  • Jordan engine, fan pump, head box or at any other'suitable point ahead of sheet formation The sheet is then formed and dried in the usual manner, thereby curing the resin to its polymerized and water-insoluble condition and imparting wet strength to the paper.
  • the cationic thermosetting resins herein disclosed impart wet strength to paper when present therein in amounts of about 0.1-% or more based on the dry weight of the paper.
  • the quantity of resin to be added to the aqueous stock suspension will depend on the degree of wet strength desired in the finished product and on the amount of resin retained by the paper fibers.
  • the uncured cationic thermosetting resins of the invention may be cured under acid, neutral or alkaline conditions, i.e., at pHs from about 4.0 to 10, by subjecting the paper to a heat-treatment for about 0.5 to 30 minutes at a temperature from about 90 to 100 C. Optimum results, however, are obtained under alkaline conditions. In view of this, and the rather extensive corrosion of equipment encountered at pHs below about 6.0, it is preferred to carry out the curing step at a pH from about 6.0 to about 9.0.
  • EXAMPLE 1 Two hundred twenty-five grams (2.18 moles) of diethylenetriamine and 100 grams of water were placed in a 3fnecked flask equipped with a mechanical stirrer, thermometer and condenser. To this was added 290 grams (2.0 moles) of adipic acid. After the acid had dissolved in the amine, the solution was heated to 185200 C. and held there for 1 /2 hours. Then vacuum from a water pump was applied to the flask during the period required for the contents of the flask to cool to 140 C. following which 430 grams of H 0 was added. The
  • polyamide solution contained 52.3% solids and had an acid number of 2.1.
  • Tacoma-bleached kraft was beaten to a Schopper- Riegler freeness of 750 cc. in a Noble and Wood cycle beater.
  • the pulp was then adjusted to pH 9.0 with V 10% NaOH and 1.0%, based on the dry weight of pulp, of the polyamide-epichlorohydrin resin, prepared as described, was added.
  • the pulp was sheeted on a. Noble and Wood handsheet machine using a closed system in which the white water contained p.p.m. sulfate ion and had been adjusted to pH 9.0 with 10% NaOH.
  • a portion of the resulting handsheets were given an additional cure of 1 hour at C.
  • the sheets were then soaked in distilled water for 2 hours and tested for wet strength. Results are listed in the table which follows Example 4.
  • EXAMPLE 2 A polyamide was prepared from 319 grams (2.18 moles) of triethylenetetramine and 290 grams (2.0 moles) of adipic acid according to the procedure described in Example 1. The polyamide solution had a pH of 10.8, an acid number of 3.2 and contained 4.98% solids.
  • EXAMPLE 3 A polyamide was prepared according to the procedure given in Example 1 using 225 grams (2.18 moles) of diethylenetriamine and 218 grams (1.5 moles) of adipic acid and 94 grams (0.5 mole) of azelaic acid. Fiftyseven and one-half grams of the polyamide solution (55% solids) were dissolved in grams of H 0 and heated to 50 C. To this were added 15 grams of epichlorohydrin over a period of 6 minutes. This solution was then heated at 6070 C. until the viscosity of the condensate reached E (Gardner). Then grams of H 0 were added and the product was cooled to 25 C. It was adjusted to pH 5.0 by adding 10 ml. of 3.7% HCl. The finished resin had a viscosity of B (Gardner) and contained 9.5% solids. It was evaluated in paper according to the procedure outlined in Example 1. Results are listed in the table following Example 4.
  • Example 1 The procedure of Example 1 was followed 'withthe (1) The reaction mixture was following exceptions. held between 180 C. and 195 C. for 45 minutes; (2) aspirator vacuum was used during this entire period; and (3) the mixture was cooled to 140 C. and diluted with 43 0 ml. of distilled water (80 0.). amide solution contained 52.4% total solids and had an acid number of 3.4.
  • Tacoma bleached kraft waterleaf sheets were tubsized (BO-second dip) in a 2.0% aqueous solution of the resin, prepared as above described, and adjusted to pH 9.0 with 10% sodium hydroxide. The sheets were squeezed (roll) and drum dried. Half were cured at 105 C. for one hour and the cured and uncured sheets then soaked in distilled water for 2 hours and tested for Mullen burst. The Mullen burst (pounds per square inchaverage of .five determinations) was 10.8 for the ,uncured sheets and 15.2 for the cured sheets as compared with a Mullen burst of less than 1 for sheets which had not been treated with the resin.
  • cell'ul'os'ic paper stock a Water-solublecationic thermosettingresin fo'rmed by"r'eactingepichlorohydrin with' a polyamide of 516 -0 saturated aliphatic' dibasic carbo'x'ylic acid and from about 0.8 'to about 1.4 moles,
  • wet-strength paper which comprises addin'g to an aqueous suspension of cellulosic paper stock a water-soluble cationic thermosett-iiig resin" formed by reacting, at a temperature from abo'ut45 C.
  • aliphatic diamine the amount'of said aliphatic diamine not exceeding 50% by weight of the polyalkylene polyamine, said polyamide containing secondary amine groups, the ratio of epichlorohydrin to secondary amine groups of said polyamide being from about 0.5 to 1 to about 1.8 to 1, adsorbing from about 0.15% of said resin on said paper stock, forming the stock so treated into a sheet, and heating the'sheet to cure the resin to a water-insoluble state.
  • a process for the production of wet-strength paper which comprises incorporating therein from about 0.1% to about 5%, based on the dry weight of the paper, of a cationic thermosetting polyamide-epichlorohydrin resin obtained by (1) reacting a C -C saturated aliphatic dibasic carboxylic acid with from about 0.8 to about 1.4 moles, per mole of dibasic carboxylic acid, of a polyalkylene polyamine at a temperature from about 110 C. to about 250 C. to form a polyamide containing secondary amine groups and (2) reacting the polyamide with epichlorohydrin at a temperature from about 45 C. to about 100 C. and at a ratio of epichlorohydrin to secondary amine groups of the polyamide of from about 0.5 to 1 to 1.8 to l to form a watersoluble cationic thermosetting resin, said resin having been cured to a water-insoluble state.
  • a cationic thermosetting polyamide-epichlorohydrin resin obtained by (1) react
  • a process for the production of wet-strength paper which comprises incorporating therein from about 0.1% to about 5%, based on the dry Weight of the paper, of a cationic thermosetting polyamide-epichlorohydrin resin obtained by (1) reacting a C -C saturated alyphatic dibasic carboxylic acid with a polyalkylene polyamine in a mole ratio of polyalkylene polyamine to dibasic acid of from about 0.8 to 1 to about 1.4 to 1 and at a temperature from about 160 C. to about 210 C. to form a polyamide containing secondary amine groups, and (2) reacting the polyamide with epichlorohydrin at a temperature from about 45 C. to about 70 C.
  • a paper product having improved wet strength comprising sheeted cellulosic fibers containing -from about 0.1% to 5%, based on its dry weight, of a cationic thermosetting polyamide-ep'ichlorohydrin resin" obtained by (1) reacting a C -C saturated aliphatic dibasic carboxylic acid with from about 0.8 to about 1.4 moles, per mole of dibasic acid, of a polyalkylene polyamine at a temperature. from about 110 C.t about 250 C. to form a polyamide containingsecondary amine groups and (2) reacting the polyamide with epichlorohydrin at a temperature from about ,45" C. to about 100 C. and at a ratio of epichlorohydrin to secondary amine groups of the polyamide of from about 0.5 to 1 to 1.8 to 1 to form a water-soluble pationic thermosetting resin, said resin having been cured to a water-insoluble state.
  • a cationic thermosetting polyamide-ep'ichlorohydrin resin
  • a paper product having improved wet strength comprising sheeted cellulosic fibers containing .from about 0.1% to 5%, based on its dry weight, of a cationic thermosetting polyamide-epichlorohydrin resin obtained by (1) reacting a 0 -0 saturated aliphatic dibasic carboxylic acid with a polyalkylene polyamineina mole ra tion of polyalkylene polyamine to dibasic acid of from about 0.8 to 1 to about 1.4 to l and at a temperature from about 160 C. to about 210 C. to form a polyamide containing secondary amine groups, and (2) reacting the polyamide with epichlorohydrin at a temperature from about C. to about C. and in a ratio of epichlorohydrin to secondary amine groups of said polyamide of from about 0,5 to 1 to about 1.8 to 1,
  • dibasic carboxylic acid is a C -C saturated aliphatic I dibasic carboxylic acid.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)
  • Polyamides (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US682086A 1921-02-24 1957-09-05 Wet-strength paper and method of making same Expired - Lifetime US2926116A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
NL231136D NL231136A (da) 1957-09-05
NL110447D NL110447C (da) 1957-09-05
US447411A US1476116A (en) 1921-02-24 1921-02-24 Electrical heating or resistance unit
US682086A US2926116A (en) 1957-09-05 1957-09-05 Wet-strength paper and method of making same
GB26945/58A GB865727A (en) 1957-09-05 1958-08-21 Improvements in or relating to resins
DE1546369A DE1546369C3 (de) 1957-09-05 1958-09-02 Verfahren zur Herstellung von Papier, Pappe und dgl. mit verbesserter Naßfestigkeit. Ausscheidung aus: 1177824
DEH34226A DE1177824B (de) 1957-09-05 1958-09-02 Verfahren zur Herstellung von wasserloeslichen Kondensaten auf Basis von Polyamiden und Epichlorhydrin
FR38672A FR1265829A (fr) 1957-09-05 1958-09-05 Perfectionnements aux résines obtenues par réaction d'un polyamide avec de l'épichlorhydrine
US796743A US2926154A (en) 1957-09-05 1959-03-03 Cationic thermosetting polyamide-epichlorohydrin resins and process of making same
US792161*A US3483077A (en) 1957-09-05 1969-01-17 Process of forming paper containing additaments and polyamide - epichlorohydrin resin

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US68208957A 1957-09-05 1957-09-05
US682086A US2926116A (en) 1957-09-05 1957-09-05 Wet-strength paper and method of making same
US69493057A 1957-11-07 1957-11-07
US694909A US3049469A (en) 1957-11-07 1957-11-07 Application of coating or impregnating materials to fibrous material

Publications (1)

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US2926116A true US2926116A (en) 1960-02-23

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US682086A Expired - Lifetime US2926116A (en) 1921-02-24 1957-09-05 Wet-strength paper and method of making same
US792161*A Expired - Lifetime US3483077A (en) 1957-09-05 1969-01-17 Process of forming paper containing additaments and polyamide - epichlorohydrin resin

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US792161*A Expired - Lifetime US3483077A (en) 1957-09-05 1969-01-17 Process of forming paper containing additaments and polyamide - epichlorohydrin resin

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US (2) US2926116A (da)
DE (2) DE1177824B (da)
FR (1) FR1265829A (da)
GB (1) GB865727A (da)
NL (2) NL110447C (da)

Cited By (229)

* Cited by examiner, † Cited by third party
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US3058873A (en) * 1958-09-10 1962-10-16 Hercules Powder Co Ltd Manufacture of paper having improved wet strength
US3066066A (en) * 1958-03-27 1962-11-27 Hercules Powder Co Ltd Mineral fiber products and method of preparing same
US3103462A (en) * 1960-04-18 1963-09-10 Eastman Kodak Co Method of improving the strength characteristics of paper prepared from partially acylated cellulose fibers
US3132944A (en) * 1960-04-18 1964-05-12 Eastman Kodak Co Photographic paper prepared from partially acylated cellulose fibers
US3146158A (en) * 1962-04-30 1964-08-25 Kimberly Clark Co Inhibiting foaming of cellulose slurries containing wet strength resins
US3186900A (en) * 1962-07-13 1965-06-01 Hercules Powder Co Ltd Sizing paper under substantially neutral conditions with a preblend of rosin and cationic polyamide-epichlorohydrin resin
US3212961A (en) * 1961-10-23 1965-10-19 Hercules Powder Co Ltd Pretreatment of paper pulp with ketene dimer in improving sizeability
US3248280A (en) * 1963-07-29 1966-04-26 Owens Illinois Inc Cellulosic and wool materials containing a reaction product of epichlorohydrin and a polyamide derived from polyalkylene polyamine with a mixture of polymeric fatty acid and dibasic carboxylic acid
US3250664A (en) * 1963-10-24 1966-05-10 Scott Paper Co Process of preparing wet strength paper containing ph independent nylon-type resins
US3278561A (en) * 1962-06-15 1966-10-11 Monsanto Co Hydrophobic diglycidylamines
US3372086A (en) * 1965-04-14 1968-03-05 Union Carbide Corp Water-soluble polyalkylenepolyamine/dialdehyde resins and application thereof in production of wet strength paper
US3372085A (en) * 1965-04-14 1968-03-05 Union Carbide Corp Water-soluble polyalkylenepolyamine/urethane resins and application thereof in production of wet strength paper
US3420735A (en) * 1967-03-31 1969-01-07 Scott Paper Co Wet-strength resins and a process for improving the wet-strength of paper
US3462383A (en) * 1966-03-07 1969-08-19 Dow Chemical Co Wet strength additives for cellulosic products
US3483077A (en) * 1957-09-05 1969-12-09 Hercules Inc Process of forming paper containing additaments and polyamide - epichlorohydrin resin
US3640840A (en) * 1968-03-27 1972-02-08 Bayer Ag Component reaction product and process for increasing the wet strength of paper
US3692092A (en) * 1968-06-13 1972-09-19 Dow Chemical Co Paper containing a polyethylenimine-fatty acid epichlorohydrin product
US3728215A (en) * 1971-03-12 1973-04-17 Hercules Inc Aminopalyamide{13 acrylamide{13 polyaldehyde resins employing an alpha, beta-unsaturated monobasic carboxylic acid or ester to make the aminopolyamide and their utility as wet and dry strengthening agents in papermaking
US3874877A (en) * 1971-07-30 1975-04-01 Fuji Photo Film Co Ltd Subbing method for photographic film support
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US3915711A (en) * 1970-08-07 1975-10-28 Fuji Photo Film Co Ltd Subbing layer photographic films with adhesive
US3962159A (en) * 1975-02-03 1976-06-08 National Starch And Chemical Corporation Graft copolymers of a polyamideamine substrate and starch, and method of making same
US3980769A (en) * 1972-09-05 1976-09-14 L'oreal Shampoo containing a water-soluble cationic polymer
US3996146A (en) * 1975-08-01 1976-12-07 Warner-Lambert Company Clear shampoo formulation
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US4109053A (en) * 1973-11-05 1978-08-22 Hercules Incorporated Sizing paper with stable dispersions of hydrocarbon resins
US4154646A (en) * 1977-07-22 1979-05-15 Hercules Incorporated Preparation of hydrophilic styrene maleic anhydride copolymer fibers for use in papermaking
US4156628A (en) * 1976-01-28 1979-05-29 Hercules Incorporated Preparation of hydrophilic polyolefin fibers for use in papermaking
US4172887A (en) * 1973-11-30 1979-10-30 L'oreal Hair conditioning compositions containing crosslinked polyaminopolyamides
US4189468A (en) * 1973-11-30 1980-02-19 L'oreal Crosslinked polyamino-polyamide in hair conditioning compositions
US4201766A (en) * 1977-03-02 1980-05-06 L'oreal Hair conditioning composition and method of using the same
US4240935A (en) * 1978-12-22 1980-12-23 Hercules Incorporated Ketene dimer paper sizing compositions
US4263182A (en) * 1979-09-06 1981-04-21 Hercules Incorporated Stable dispersions of fortified rosin
US4273892A (en) * 1974-11-05 1981-06-16 Hercules Incorporated Preparation of hydrophilic polyolefin fibers for use in papermaking
US4277581A (en) * 1973-11-30 1981-07-07 L'oreal Polyamino-polyamide crosslinked with crosslinking agent
US4317756A (en) * 1977-08-19 1982-03-02 Hercules Incorporated Sizing composition comprising a hydrophobic cellulose-reactive sizing agent and a cationic polymer
US4347339A (en) * 1981-05-08 1982-08-31 Nalco Chemical Company Cationic block copolymers
JPS58146408A (ja) * 1982-02-05 1983-09-01 ポ−ル・コ−ポレ−シヨン 制御された表面性状を有するポリアミドメンブラン
WO1984003055A1 (en) 1983-02-07 1984-08-16 Univ Yale Transfer of macromolecules from a chromatographic substrate to an immobilizing matrix
US4473474A (en) * 1980-10-27 1984-09-25 Amf Inc. Charge modified microporous membrane, process for charge modifying said membrane and process for filtration of fluid
US4478682A (en) * 1981-07-02 1984-10-23 Hercules Incorporated Sizing method and sizing composition for use therein
DE3328463A1 (de) * 1983-08-06 1985-02-21 Felix Schoeller jr. GmbH & Co KG, 4500 Osnabrück Fotografischer papiertraeger
US4523995A (en) * 1981-10-19 1985-06-18 Pall Corporation Charge-modified microfiber filter sheets
US4673504A (en) * 1980-10-27 1987-06-16 Cuno Inc. Charge modified microporous membrane
US4689374A (en) * 1983-06-09 1987-08-25 W. R. Grace & Co. Water soluble polyamidoaminepolyamine having weight average molecular weight of at least 5×105
US4708803A (en) * 1980-10-27 1987-11-24 Cuno Incorporated Liquid filtration using hydrophilic cationic isotropic microporous nylon membrane
US4711793A (en) * 1980-10-27 1987-12-08 Cuno Incorporated Process for charge modifying a microphorous membrane
US4714736A (en) * 1986-05-29 1987-12-22 The Dow Chemical Company Stable polyamide solutions
US4722964A (en) * 1986-06-20 1988-02-02 Borden, Inc. Epoxidized polyalkyleneamine-amide wet strength resin
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GB865727A (en) 1961-04-19
DE1546369B2 (de) 1974-04-04
FR1265829A (fr) 1961-07-07
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DE1546369A1 (de) 1970-05-21
DE1177824B (de) 1964-09-10
US3483077A (en) 1969-12-09
DE1546369C3 (de) 1974-11-21

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