WO2000078717A1 - Agents d'encollage dotes de proprietes performantes accrues - Google Patents

Agents d'encollage dotes de proprietes performantes accrues Download PDF

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Publication number
WO2000078717A1
WO2000078717A1 PCT/US2000/017428 US0017428W WO0078717A1 WO 2000078717 A1 WO2000078717 A1 WO 2000078717A1 US 0017428 W US0017428 W US 0017428W WO 0078717 A1 WO0078717 A1 WO 0078717A1
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WIPO (PCT)
Prior art keywords
primary amino
molecule
sizing agent
cyclic imide
amino groups
Prior art date
Application number
PCT/US2000/017428
Other languages
English (en)
Inventor
Patrick C. Hu
Valerie N. Legloahec
Dixie E. Goins
Original Assignee
Albemarle Corporation
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Publication of WO2000078717A1 publication Critical patent/WO2000078717A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • 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
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/16—Sizing or water-repelling agents
    • 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
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/07—Nitrogen-containing compounds
    • 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
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/14—Carboxylic acids; Derivatives thereof
    • D21H17/15—Polycarboxylic acids, e.g. maleic acid
    • D21H17/16—Addition products thereof with hydrocarbons
    • 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
    • D21H17/71—Mixtures of material ; Pulp or paper comprising several different materials not incorporated by special processes
    • D21H17/72—Mixtures of material ; Pulp or paper comprising several different materials not incorporated by special processes of organic material

Definitions

  • This invention relates to, and has as one of its objectives, the provision of new bromine-containing sizing agents for paper and paper products.
  • one or a mixture of aromatic halogen-containing cyclic imides formed from one or a mixture of halophthahc anhydrides and at least one aliphatic amine having one or two primary amino groups in the molecule. If there is only one primary amino group in the aliphatic amine reactant(s), the resultant compound(s) of this invention will contain one halogen-containing aromatic ring in the molecule.
  • a second embodiment of this invention is a mixture of aromatic halogen-containing cyclic imides and aromatic non-halogen-containing cyclic imides formed from the combination of (a) one or more halophthahc anhydrides together with phthalic anhydride, and
  • this invention provides one or a mixture of aromatic halogen-containing cyclic imides in which there are two different cyclic imide moieties in the molecule.
  • One such moiety is formed by reaction of a halophthahc anhydride with one of the primary amino groups of an aliphatic amine having two primary amino groups in the molecule.
  • the other such moiety is formed by reaction of the other primary amino group with an alkenyl or alkyl succinic anhydride.
  • the sequence of these two reactions is not critical ⁇ either one can precede the other.
  • the cyclic imides of this third embodiment are thus asymmetrical bis-imides.
  • a fourth embodiment of this invention provides mixtures of at least one compound of the first embodiment and at least one compound of the third embodiment of this invention.
  • a fifth embodiment of this invention provides mixtures of (a) a mixture of compounds of the second embodiment and (b) at least one compound of the third embodiment of this invention.
  • the mixtures of the fourth and fifth embodiments can have the components thereof in any proportions.
  • the compounds of this invention can have from one to four halogen atoms on each aromatic ring present in the molecule.
  • the halogen atom(s) on the aromatic ring(s) of the compounds of this invention can be any halogen atom, but preferably is fluorine, chlorine, or bromine, and most preferably is fluorine or bromine.
  • the aromatic ring will contain either two or four halogen atoms.
  • Preferred aliphatic amines used in forming the above succinimide(s) are alkyl or alkenyl primary monoamines, alpha omega alkylene diamines, alkylene polyamines having two terminal primary amino groups and at least one internal secondary amino group, and alkylene polyamines having one terminal primary amino group and at least one secondary or tertiary amino group.
  • the cyclic imides of this invention can be composed of one single compound meeting the above requirements, or they can be a mixture of two or more compounds meeting the above requirements.
  • the imides of this invention are in the form of a mixture of compounds of the third embodiment described above, the mixture can differ in various respects. In one case, the mixture can differ only in the chain lengths of the alkenyl and/or alkyl groups in the moiety derived from the alkenyl and/or alkyl succinic anhydrides.
  • the mixture of compounds of the third embodiment can be made from a mixture of two or more species of one type of amine having two primary amino groups in the molecule (e.g., a mixture of, say, ethylene diamine and hexamethylene diamine, or a mixture of, say, diethylene triamine, triethylene tetramine, and tetraethylene pentamine).
  • the mixture of compounds of the third embodiment can be made from a mixture of at least two different types of amines having two primary amino groups in the molecule (e.g., a mixture, say, of 1,4-butane diamine and diethylene triamine).
  • the components of mixtures of the third embodiment can also differ in the manner of more than one of the foregoing cases.
  • the overall mixture can contain (i) components which differ in the chain lengths of the alkenyl or alkyl groups in the moiety derived from the alkenyl and/or alkyl succinic anhydrides used and (ii) other components which differ in the identities of the amines used having two primary amino groups in the molecule.
  • the various imide(s) of this invention described above is one or a mixture of such compounds which is a solid at room temperature (e.g. , in the range of 20 to 25 ° C) and which has a melting temperature no higher than 120 ° C, and preferably no higher than 100 °C.
  • a further embodiment of this invention provides improvements in the sizing of cellulosic pulp in an aqueous medium.
  • this invention provides, in a process of sizing a cellulose fiber in an aqueous paper-making slurry, the improvement which comprises introducing into said slurry as a sizing agent at least one halogen-containing cyclic imide of this invention.
  • Such a process is often referred to in the art as an internal sizing process.
  • Still another embodiment of this invention provides improvements in the external sizing of paper products. More particularly, in a process wherein a sizing agent is applied to the surface of a paper web and is impressed thereon under pressure, this invention provides the improvement wherein the sizing agent comprises at least one halogen-containing cyclic imide of this invention. Typically, such sizing agent is applied to either or both sides of the web either in the form of one or more aqueous sprays in which the sizing agent has been suitably emulsified or by use of a size press wherein an aqueous emulsion of the sizing agent is maintained in the flooded nip of the press through which the web is passed.
  • a feature of this invention is that the halogen-containing cyclic imides provided pursuant to this invention when properly used are highly effective both in internal sizing operations and in external sizing operations. Typically these sizing operations are conducted in the presence of at least one filler and/or at least one pigment, such as precipitated calcium carbonate, titanium dioxide, clay, or the like.
  • the particular way in which the halogen-containing cyclic imide sizing agent is utilized for internal or external sizing is not relevant to this invention, because the imide(s) of this invention can be used in virtually any known kind of cellulosic or paper sizing operation.
  • a suitable sizing amount of one or more halogen- containing cyclic imides of this invention is/are brought into contact with the substrate to be sized and the sizing agent is caused to react therewith.
  • the imide(s) of this invention can be used as the sole sizing agent, or such imide(s) can be used in combination with other suitable pulp or paper sizing agents, such as an alkenyl succinic anhydride sizing agent or a ketene dimer sizing agent.
  • the preferred sizing agents of this invention have a viscosity of no more than about 220 centistokes at 80°C.
  • a feature of the sizing agents of this invention is that they possess the capability of rendering paper products sized therewith more flame resistant than in the absence of such treatment.
  • any halophthahc anhydride can be made as one of the reactants of any halophthahc anhydride.
  • use can be made of mono, di, tri, and/or tetrahalophthalic anhydrides either singly or in combination.
  • Preferred are dihalophthalic anhydrides and tetrahalophthalic anhydrides.
  • the halogen atoms are typically fluorine, chlorine or bromine atoms, with fluorine or bromine substitutions being prefened.
  • alkyl or alkenyl primary monoamines are preferred.
  • Such amines will typically contain in the range of from 4 to 30 carbon atoms in the molecule.
  • Such amines are exemplified by such compounds as, for example, n-butylamine, n-pentylamine, n-hexylamine, n-heptylamine, n- octylamine, and their higher homologs having up to about 30 carbon atoms in the molecule, and their olefinically unsaturated analogs such as oleylamine. Mixtures of two or more such amines can be used.
  • amines those having in the range of 10 to 26 carbon atoms in the molecule or mixtures thereof are preferred.
  • Other amines containing only one primary amino group in the molecule are exemplified by such compounds as N,N-diethyl-diethylene triamine, N,N-dimethyl- triethylene tetramine, and analogous compounds, and mixtures thereof.
  • Aliphatic diamines which can be used in forming the sizing agents of this invention include alkylene diamines having in the range from 2 up to 14 carbon atoms and preferably up to 10 carbon atoms per molecule.
  • alkylene diamines having in the range from 2 up to 14 carbon atoms and preferably up to 10 carbon atoms per molecule.
  • examples of such compounds include ethylene diamine, propylene diamine (1 ,3-propanediamine), butylene diamine ( 1 ,4-butane diamine), 1 ,5-pentane diamine, hexamethylene diamine (1,6-hexane diamine), and their higher homo logs.
  • alkylene polyamines which typically contain from 3 to 15 and preferably from 3 to 10 nitrogen atoms per molecule and from 4 to 30 and preferably 4 to 20 carbon atoms per molecule.
  • alkylene polyamines which typically contain from 3 to 15 and preferably from 3 to 10 nitrogen atoms per molecule and from 4 to 30 and preferably 4 to 20 carbon atoms per molecule.
  • Such compounds are exemplified by diethylene triamine, triethylene tetramine, tetraethylenepentamine, pentaethylenehexamine, and their higher homologs and branched chain analogs.
  • the amines having two primary amino groups in the molecule can be used either as individual compounds or as mixtures of compounds in forming the imides of this invention.
  • an alkenyl or alkyl succinic anhydride is reacted with the product formed from reaction between one equivalent of a halophthahc anhydride and one equivalent of an aliphatic amine having two primary amino groups in the molecule.
  • the preliminary reaction between the halophthahc anhydride and the aliphatic amine results in the cyclic imide formation with one of the two amino groups of the aliphatic amine.
  • the second amino group of the aliphatic amine is reacted with the alkenyl or alkyl succinic anhydride to form the bis-imide of the third embodiment of this invention.
  • the bis-imide of the third embodiment can be formed by reversing this order of reaction. More particularly, a preliminary reaction is conducted in which one equivalent of an alkenyl or alkyl succinic anhydride is reacted with one equivalent of an aliphatic amine having two primary amino groups in the molecule to thereby form a monoimide. This monoimide is then reacted with a halophthahc anhydride or mixture of halophthahc anhydrides to produce the bis-imide of the third embodiment of this invention. Any alkenyl or alkyl succinic anhydride of suitable chain length can be used in the reactions described in the immediately preceding paragraph.
  • alkenyl succinic anhydride can be formed by an ene reaction between one or more alpha-olefins and maleic anhydride, by an ene reaction between one or more internal olefins and maleic anhydride, or by an ene reaction between a mixture of one or more internal and one or more alpha-olefins.
  • these olefins are linear or substantially linear olefins.
  • Most preferred are internal olefins which are linear or which have at most one methyl or methylene side chain in the molecule.
  • Such olefins can be prepared by the isomerization of linear alpha-olefins which in turn are usually produced either by ethylene chain growth technology or by thermal cracking of paraffin waxes.
  • Ethylene chain growth processing typically involves use of an aluminum alkyl notably tri ethyl aluminum, and this results in the preparation of alpha-olefins having even numbers of carbon atoms in the molecule.
  • Isomerization of alpha-olefins to internal olefins is best carried out by catalytic photo initiated isomerization of the alpha-olefins to internal olefins using iron pentacarbonyl as the catalyst.
  • iron pentacarbonyl as the catalyst.
  • Illustrative internal olefins which can be used in forming the alkenyl succinic anhydride intermediates include, for example, 2-tetradecene, 3-tetradecene, 4-tetradecene, 5- tetradecene, 6-tetradecene, 7-tetradecene, 2-pentadecene, 3-pentadecene, 4-pentadecene, 5- pentadecene, 6-pentadecene, 7-pentadecene, and their higher homologs and straight chain analogs having up to about 30 carbon atoms per molecule, 5-methyl-tridec-4-ene, 5-methyl- tridec-5-ene, 3-methyl-tridec-2-ene, 3-methyl-tridec-3-ene, and their higher homologs and analogs having up to about 30 carbon atoms per molecule.
  • alkenyl succinic anhydride intermediates As noted above, individual internal olefins meeting these structural requirements can be employed as raw materials in the synthesis of the alkenyl succinic anhydride intermediates. Alternatively, mixtures of such internal olefins can be employed.
  • Illustrative alpha olefins which can be used alone or in combination with such internal olefins in forming the alkenyl succinic anhydride intermediates include, for example, 1-tetradecene, 1 -pentadecene, 1-hexadecene, 1- heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, and their higher homologs having up to about 30 carbon atoms per molecule.
  • Alpha-olefins used in forming the preferred internal olefins used in producing alkenyl succinic anhydride intermediates are formed by chain growth of ethylene using process technology such as described in U.S. Pat. Nos. 3,391,175 and 3,391,219. Methods for conducting the ene reaction are well known and are reported in the literature.
  • the process is a thermal process, and if desired one or more additives can be included in the reaction mixture to inhibit color tar, or polymer formation during the thermal process. See, for example, U.S. Pat. Nos. 4,958,034 and 5,021,169 and references cited therein, for details concerning the thermal process and use of additives therein to inhibit tar and color formation.
  • the use of such additives may not be required, however, especially if the process is performed at a temperature in the range of 240 to 250 °C using an excess of olefin, and the reaction is terminated before reaching complete conversion.
  • Alkenyl succinic anhydride or mixtures of alkenyl succinic anhydrides prepared from polymers such as polyethylene, polypropylene, polybutylene, or polyisobutylene can be used but generally are less preferable.
  • alkenyl succinic anhydride(s) is/are subjected to hydrogenation under a pressurized hydrogen atmosphere in the presence of a suitable catalyst such as palladium on charcoal.
  • a suitable catalyst such as palladium on charcoal.
  • One way involves hydrogenating the alkenyl group of the succinimide formed by reacting one equivalent of the alkenyl succinic anhydride with one equivalent of an aliphatic amine having two primary amino groups in the molecule.
  • the other way involves hydrogenating the alkenyl group of the bis-imide formed pursuant to the third embodiment of this invention described above.
  • the sizing agent(s) is utilized in the form an aqueous emulsion.
  • Methods and materials for accomplishing such emulsification are well known and reported in the literature.
  • succinimides of this invention Because of the particular structural characteristics and physical properties possessed by the succinimides of this invention, they can be effectively utilized in both internal and in external sizing operations. In both such operations, an advantage of their use is their superior hydrolytic stability.
  • Example 1 describes a procedure for the synthesis of dibromophthalic anhydride.
  • Example 2 is a general procedure for producing alkenyl succinic anhydride. A procedure for conducting imidization reactions is described in Example 3.
  • reaction is exothermic and the reaction temperature rises to about 78 ° C at the end of this addition.
  • Solid products start separating from the solution when about one-half of the dibromodimethyl hydantoin has been added, but a considerable amount remains dissolved in the sulfuric acid.
  • the reaction slurry is stirred for an additional hour while allowing it to cool during this time to about 40 ° C.
  • the reaction slurry is then diluted with 61 g of ice/cold water and stirred for an additional 15 minutes. External cooling is applied during this operation to contain the heat generated.
  • the product is recovered by filtration.
  • the product produced in this manner typically contains a mixture of isomers.
  • a nitrogen-dried stainless steel reactor equipped with a mechanical stiner, a thermocouple well, and a nitrogen inlet tube, was charged with the selected olefin or mixture of olefins used for producing the particular alkenyl succinic anhydride intermediate to be used for preparing the ultimate succinimide of this invention.
  • maleic anhydride Into the reactor were charged maleic anhydride and the olefin or mixture of olefins in proportions of 1.5 to 2 equivalent(s) of the olefin(s) per equivalent of maleic anhydride.
  • the vessel was then bolted to the reactor frame, and the reaction mixture was purged with nitrogen for approximately 15 minutes.
  • Heat was applied to the reaction mixture either by means of an electrical mantle or by means of a circulating hot oil bath and when the temperature reached approximately 50-60 °C stirring was initiated.
  • the stirrer used was a double helical impeller operated at approximately 900 rpm.
  • the reaction was conducted at temperatures in the range of about 220-230 °C for periods in the range of about 2-6 hours.
  • the reaction mixture was quickly discharged through the bottom valve of the reactor into a suitable Erlenmeyer flask under a nitrogen atmosphere. Unreacted olefin and maleic anhydride were stripped from the reaction mixture under reduced pressure. The reaction mixtures were then further purified by distillation under reduced pressure.
  • a 100-mL round bottom flask equipped with a Dean-Stark trap, a condenser and a magnetic stirrer was charged with 1 equivalent of a halophthahc anhydride or an alkenyl succinic anhydride, a solvent quantity of xylene, 1-2 drops of concentrated sulfuric acid, and 1 equivalent of the selected amine having one primary amino group in the molecule or the selected amine having two primary amino groups in the molecule.
  • the reaction mixture is then stirred and heated at reflux (approximately 140°C) with continuous removal of water until the theoretical amount of water was released or until no further formation of water occurred.
  • the progress of the reaction can be monitored by infrared specfroscopy.
  • the reaction mixture is cooled to room temperature.
  • the reaction time is in the range of about 1-2 hours.
  • xylene is removed by distillation under reduced pressure. The resulting yellow or brown viscous liquids or semi- solids are used without further purification. NMR and IR analyses of the products can be used to verify product purity.
  • Example 3 When preparing a mixed bis-imide of the third embodiment of this invention, the procedure of Example 3 is carried out using an amine having two primary amino groups and either the halophthahc anhydride or the alkenyl succinic anhydride. After the resulting monoimide product has been formed, this product is then used as the reactant in a similar imidization reaction using the other of the two types of anhydride.
  • acylating agents corresponding to maleic anhydride can be used in preparing the alkenyl succinic anhydrides used in forming the bis-imides of the third embodiment of this invention.
  • maleic acid, the mono or dimethyl ester thereof, or the acid chlorides thereof can be used in lieu of, or in addition to, maleic anhydride. Because of its excellent reactivity, use of maleic anhydride itself is preferred.
  • acylating agents closely related to maleic anhydride such as citraconic anhydride, itaconic anhydride, dimethyl maleic anhydride, and their corresponding acids, lower alkyl esters, or acid halides in lieu of or in addition to maleic anhydride.

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  • Organic Chemistry (AREA)
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Abstract

L'invention concerne des agents d'encollage comprenant au moins dans leur molécule une fraction imide cyclique aromatique contenant halogène. On forme un tel type d'agent à partir d'au moins un anhydride halophtalique et d'au moins une amine aliphatique possédant dans sa molécule un ou deux groupes amino primaires. L'invention concerne un autre type de mélange constitué de (a) au moins un imide cyclique aromatique contenant halogène et formé à partir d'au moins un anhydride halophtalique et d'au moins une amine aliphatique possédant dans sa molécule un ou deux groupes amino primaires, et (b) au moins un imide cyclique aromatique dépourvu d'halogène et formé à partir d'anhydride phtalique et au moins une amine aliphatique possédant dans sa molécule un ou deux groupes amino primaires. L'invention concerne encore un autre type de mélange composé d'au moins un imide bis-cyclique dans la molécule duquel se trouvent deux fractions imides cycliques différentes, (a) une fraction formée par réaction d'un équivalent d'un anhydride halophtalique avec un équivalent d'un groupe amino primaire, et (b) l'autre fraction formée par réaction d'un équivalent d'un anhydride succinique d'alcényle ou d'alkyle avec un équivalent d'un groupe amino primaire, les deux groupes amino primaires étant présents dans une amine aliphatique possédant dans sa molécule deux et seulement deux groupes amino primaires. L'invention concerne encore des procédés d'utilisation de telles substances en tant qu'agents d'encollage intérieur ou extérieur.
PCT/US2000/017428 1999-06-24 2000-06-22 Agents d'encollage dotes de proprietes performantes accrues WO2000078717A1 (fr)

Applications Claiming Priority (4)

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US14078199P 1999-06-24 1999-06-24
US60/140,781 1999-06-24
US59564100A 2000-06-16 2000-06-16
US09/595,641 2000-06-16

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1422302A (en) * 1973-01-31 1976-01-28 Bayer Ag Copolymer salts suitable for use in anionic sizes
US3993640A (en) * 1973-12-21 1976-11-23 Laporte Industries Limited Treatment of cellulosic materials
JPS5428389A (en) * 1977-08-05 1979-03-02 Kuraray Co Ltd Preparation of modified polyvinyl alcohol-type polymer
GB1588416A (en) * 1976-09-08 1981-04-23 Laporte Industries Ltd Process and compositions for the treatment of cellulosic materials
GB2082067A (en) * 1980-08-22 1982-03-03 Nitrokemia Ipartelepek Antidote-containing herbicidal compositions
US5114538A (en) * 1988-06-21 1992-05-19 Exxon Chemical Patents Inc. Process for sizing paper and similar products
JPH0539390A (ja) * 1991-08-02 1993-02-19 Idemitsu Petrochem Co Ltd エンジンアンダーカバー

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1422302A (en) * 1973-01-31 1976-01-28 Bayer Ag Copolymer salts suitable for use in anionic sizes
US3993640A (en) * 1973-12-21 1976-11-23 Laporte Industries Limited Treatment of cellulosic materials
GB1588416A (en) * 1976-09-08 1981-04-23 Laporte Industries Ltd Process and compositions for the treatment of cellulosic materials
JPS5428389A (en) * 1977-08-05 1979-03-02 Kuraray Co Ltd Preparation of modified polyvinyl alcohol-type polymer
GB2082067A (en) * 1980-08-22 1982-03-03 Nitrokemia Ipartelepek Antidote-containing herbicidal compositions
US5114538A (en) * 1988-06-21 1992-05-19 Exxon Chemical Patents Inc. Process for sizing paper and similar products
JPH0539390A (ja) * 1991-08-02 1993-02-19 Idemitsu Petrochem Co Ltd エンジンアンダーカバー

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 197915, Derwent World Patents Index; Class A14, AN 1979-28478B, XP002144389 *
DATABASE WPI Section Ch Week 199312, Derwent World Patents Index; Class A95, AN 1993-096854, XP002144388 *

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