US3223550A - Process for rendering thermoplastic fibers paper translucent - Google Patents

Process for rendering thermoplastic fibers paper translucent Download PDF

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Publication number
US3223550A
US3223550A US166671A US16667162A US3223550A US 3223550 A US3223550 A US 3223550A US 166671 A US166671 A US 166671A US 16667162 A US16667162 A US 16667162A US 3223550 A US3223550 A US 3223550A
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US
United States
Prior art keywords
percent
paper
acrylonitrile
solution
vinyl
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
US166671A
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English (en)
Inventor
Julian J Hirshfeld
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.)
Monsanto Co
Original Assignee
Monsanto 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
Priority to NL287794D priority Critical patent/NL287794A/xx
Priority to BE627201D priority patent/BE627201A/xx
Application filed by Monsanto Co filed Critical Monsanto Co
Priority to US166671A priority patent/US3223550A/en
Priority to CH38563A priority patent/CH424459A/fr
Priority to GB1520/63A priority patent/GB1029944A/en
Priority to DK18263AA priority patent/DK104605C/da
Priority to FR921430A priority patent/FR1343414A/fr
Application granted granted Critical
Publication of US3223550A publication Critical patent/US3223550A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • 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
    • Y10T428/31935—Ester, halide or nitrile of addition polymer

Definitions

  • This invention is concerned with rendering paper composed of thermoplastic fibers translucent to light. More particularly this invention is concerned with rendering paper composed of acrylic fibers translucent to light.
  • An object of this invention is to produce translucent paper composed of synthetic fibers. Another object of this invention is to produce translucent paper composed of acrylic fibers. Other objects of this invention will be apparent from the following detailed description and claims.
  • the objectives of this invention are accomplished by treating paper composed of thermoplastic fibers with an aqueous solution of tris(2,3-dibromopropyl)phosphate, phosphorous acid and phytic acid.
  • the paper composed of synthetic fibers as described in a copending application, filed August 10, 1959, SN. 832,466, and now U.S. Patent No. 3,047,- 450, March 16, 1961, SN. 96,108, now abandoned, is padded with an aqueous or alcohol solution of the above identified agents varying from 5 percent to a 100 percent solution with the preferred being a 50 percent solution which includes any conventional solvent for the given compound such as aliphatic alcohols, benzene, toluene, etc.
  • the sheets of paper are immersed in a solution, as described hereinbefore, of the agents for from 5 seconds to 15 minutes with the preferred being around 3 minutes more or less.
  • the paper is then dried at any convenient temperature, such as 90 C. in a conventional drying oven, being sure not to heat to the discoloration point of the acrylic fibers Which is 165 C.
  • the paper may be used in windows to admit light but not images, such as in homes in Japan or in any place where light is required or desired, but no images; it may be used as tracing paper by anyone but especially engineers and architects; it may be used as a wrapper for anything which one may wish to tell what is inside the wrapping and many other uses as Well and it may be used for lamp shades.
  • the fibers which go to make up the paper of this invention are poly-acrylonitrile, copolymers, including binary and ternary polymers containing at least 80 percent by weight of acrylonitrile in the polymer molecule, or a blend comprising polyacrylonitrile or copolymers comprising acrylonitrile with from 2 to 50 percent of another polymeric material, the blend having an overall polymerized acrylonitrile content of at least 80 percent by weight.
  • the preferred polymers employed in the instant invention are those containing at least 80 percent of acrylonitrile, generally recognized as the fiber-forming acrylonitrile polymers, it will be understood that the invention is likewise applicable to polymers containing less than 80 percent acrylonitrile.
  • the acrylonitrile polymers containg less than 80 percent acrylonitrile are useful in forming films, coating compositions, molding operation and lacquers.
  • the polymer may be a copolymer of from 80 to 98 percent acrylonitrile and from 2 to 20 percent of another monomer containing the C C linkage and copolymerizable with acrylonitrile.
  • Suitable monoolefinic monomers include acrylic, alpha-chloroacrylic and methacrylic acids; methoxylmethyl methacrylate, beta-chloro- 3,223,550 Patented Dec.
  • the polymer may be a ternary or higher interpolymer, for example, products obtained by the interpolymerization of acrylonitrile and two or more of any of the monomers, other than acrylonitrile enumerated above. More specifically, and preferably the ternary polymer comprises acrylonitrile, methacrylonitrile, and 2-vinylpyridine.
  • the ternary polymers preferably contain from to 98 percent of acrylonitrile, from 1 to 10 percent of a vinylpyridine or a l-vinylimidazole, and from 1 to 18 percent of another substance such as methacrylonitrile or vinyl chloride.
  • the polymer may also be a blend of a polyacrylonitrile or of a binary .interpolymer of from 80 to 99 percent acrylonitrile and from 1 to 20 percent of at least one other C C containing substance with from 2 to 50 percent of the weight of the blend of a copolymer of from 10 to 70 per-cent of acrylonitrile and from 30 to 90 percent of at least one other C:C containing polymerizable monomer.
  • the polymeric material when it comprises a blend, it will be a blend of a copolymer of 90 to 98 percent acrylonitrile and from 2 to 10 percent of another mono-olefinic momomer, such as vinyl acetate with a sufiicient amount of a copolymer of from 10 to 70 percent of acrylonitrile and from 30 to 90 percent of a vinyl-substituted tertiary heterocyclic amine, such as vinylpyridine or -1-vinylimidazole, to give a dyeable blend having an overall vinyl-substituted tertiary heterocyclic amine content of from 2 to 10 percent based on the weight of the blend.
  • a copolymer of 90 to 98 percent acrylonitrile and from 2 to 10 percent of another mono-olefinic momomer such as vinyl acetate
  • Example 1 A piece of paper composed of a blend of percent of a polymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 15 percent of cellulose acetate, was immersed in a solution of 8 grams of tris-(2,3-dibromopropyl)phosphate and 12 grams of methyl alcohol. The paper was kept in the solution for 3 minutes and then removed and dried under a hood. After being dried, the paper was compared with an untreated piece of paper, and the treated paper possessed good translucent properties in comparison to the untreated paper.
  • Example 2 A piece of paper composed of a blend of 85 percent of a polymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 15 percent of cellulose acetate, was immersed in a solution of 10 grams of tris-(2,3-dibromopropyl)phosphate and 10 grams of methyl alcohol. The piece of paper was kept in the solution for 3 minutes and then dried under a hood. After being dried, the paper was compared with an untreated piece and the treated paper possessed superior translucent properties.
  • Example 3 A piece of paper composed of a blend of 85 percent of a polymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 15 percent of cellulose acetate, was immersed in a solution of 12 grams of tris-(2,3-dibromopropyl)phosphate and 8 grams of methyl alcohol. The paper was kept in the solution for 3 minutes and then removed and dried under a hood. After being dried the paper was compared with an untreated piece of paper, and the treated paper possessed excellent translucent properties in comparison to the untreated paper.
  • Example 4 A piece of paper composed of a blend of 85 percent of a polymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 15 percent of cellulose acetate, was immersed in a solution of 20 grams of concentrated phosphoric acid, assay 85 percent to 87 percent. The paper was kept in the solution for 3 minutes and then removed and dried under a hood. After being dried, the paper was compared with an untreated piece of paper, and the treated paper possessed superior translucent properties in comparison to the untreated paper.
  • Example 5 A piece of paper composed of a blend of 85 percent of a polymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 15 percent of cellulose acetate, was immersed in a solution of 15 grams of concentrated phosphoric acid, assay 85 percent to 87 percent, and 5 grams of water. The paper was kept in the solution for 3 minutes and then removed and dried under a hood. After being dried, the paper was compared with an untreated piece of paper, and the treated paper possessed good translucent properties in comparison to the untreated paper.
  • Example 6 A piece of paper composed of a blend of 85 percent of a polymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 15 percent cellulose acetate, was immersed in a solution of 20 grams of concentrated phytic acid, assay 70 percent. The paper was kept in the solution for 3 minutes and then removed and dried under a hood. After being dried, the paper was compared with an untreated piece of paper, and the treated paper possessed superior translucent properties in comparison to the untreated paper.
  • Example 7 A piece of paper composed of a blend of 85 percent of a polymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 15 percent cellulose acetate, was immersed in a solution of 15 grams of concentrated phytic acid, assay 70 percent, and 5 grams of water. The paper was kept in the solution for 3 minutes and then removed and dried under a hood. After being dried, the paper was compared with an untreated piece of paper, and the treated paper possessed superior translucent properties in comparison to the untreated paper.
  • Example 8 A piece of paper composed of fibers of a blend of 88 percent of one copolymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 12 percent of another copolymer of 50 percent acrylonitrile and 50 percent methyl vinyl pyridine was immersed in a solution of 8 grams of tris(2,3-dibromopropyl)phosphate and 12 grams of methyl alcohol. The paper was kept in the solution for 3 minutes and then removed and dried in a hood. After being dried, the paper was compared with an untreated piece of paper and the treated paper possessed good translucent properties in comparison to the untreated paper.
  • Example 9 The exact process of Example 8 was repeated except the solution was composed of 10 grams of tris(2,3-dibromopropyl)phosphate and 10 grams of methyl alcohol. This treated paper possessed good translucent properties when compared to an untreated sample of paper.
  • Example 10 The exact process of Example 8 was repeated except the solution was composed of 12 grams of tris(2,3-dibromopropyl)phosphate and 8 grams of methyl alcohol. This treated paper possessed superior translucent properties when compared to an untreated sample of paper.
  • An article composed of paper of acrylic fibers and a translucidizing agent selected from the group consisting of tris(2,3-dibromopropyl)phosphate, phosphoric acid and phytic acid.
  • a translucidizing agent selected from the group consisting of tris(2,3-dibromopropyl)phosphate, phosphoric acid and phytic acid.
  • translucidizing agent is tris(2,3-dibromopropyl)phosphate.
  • translucidizing agent is tris(2,3-dibromopropyl)phosphate.
  • the article of claim 11 in which the paper is composed of percent by weight of fibers of copolymers of 94 percent by Weight of acrylonitrile and 6 percent by weight of vinyl acetate, and 15 percent by weight of fibers of cellulose acetate.
  • a method of rendering translucent paper composed of a blend of a fiber of 85 percent of 94 percent acrylonitrile and 6 percent vinyl acetate and 15 percent of cellulose acetate, comprising treating said paper with a 50 percent solution of tris(2,3-dibromopropyl)phosphate and methyl alcohol, removing said paper from said solution and drying same.
  • a method of rendering translucent paper composed of acrylic fibers which comprises impregnating said paper with a solution of a translucidizing agent selected from the group consisting of tr-is(2,3-dibromopropyl)phosphate, phosphoric acid and phytic acid and drying said treated paper.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)
US166671A 1962-01-16 1962-01-16 Process for rendering thermoplastic fibers paper translucent Expired - Lifetime US3223550A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL287794D NL287794A (en(2012)) 1962-01-16
BE627201D BE627201A (en(2012)) 1962-01-16
US166671A US3223550A (en) 1962-01-16 1962-01-16 Process for rendering thermoplastic fibers paper translucent
CH38563A CH424459A (fr) 1962-01-16 1963-01-11 Papier translucide composé de fibres thermoplastiques et procédé de fabrication de ce papier
GB1520/63A GB1029944A (en) 1962-01-16 1963-01-14 Translucent paper and method of making it
DK18263AA DK104605C (da) 1962-01-16 1963-01-15 Fremgangsmåde til at gøre papir, bestående af fibre af acrylonitrilpolymere eller -copolymere fortrinsvis indeholdende mindst 80% polymeriseret acrylonitril og indtil 15% celluloseacetat, lysgennemskinneligt.
FR921430A FR1343414A (fr) 1962-01-16 1963-01-15 Papiers translucides composés de fibres thermoplastiques et leur fabrication

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US166671A US3223550A (en) 1962-01-16 1962-01-16 Process for rendering thermoplastic fibers paper translucent

Publications (1)

Publication Number Publication Date
US3223550A true US3223550A (en) 1965-12-14

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Family Applications (1)

Application Number Title Priority Date Filing Date
US166671A Expired - Lifetime US3223550A (en) 1962-01-16 1962-01-16 Process for rendering thermoplastic fibers paper translucent

Country Status (6)

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US (1) US3223550A (en(2012))
BE (1) BE627201A (en(2012))
CH (1) CH424459A (en(2012))
DK (1) DK104605C (en(2012))
GB (1) GB1029944A (en(2012))
NL (1) NL287794A (en(2012))

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2268556A (en) * 1939-01-06 1942-01-06 Du Pont Fire retardant textile
US2660543A (en) * 1948-11-26 1953-11-24 Glenn L Martin Co Flameproofing polymers
US2665983A (en) * 1948-08-02 1954-01-12 Shell Dev Method of sizing paper
US3047456A (en) * 1959-08-10 1962-07-31 Monsanto Chemicals Manufacture of paper products from fibers wet spun from polymer blends
US3058941A (en) * 1959-12-14 1962-10-16 Monsanto Chemicals Compositions comprising an organic polymer and an organo phosphorus compound

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2268556A (en) * 1939-01-06 1942-01-06 Du Pont Fire retardant textile
US2665983A (en) * 1948-08-02 1954-01-12 Shell Dev Method of sizing paper
US2660543A (en) * 1948-11-26 1953-11-24 Glenn L Martin Co Flameproofing polymers
US3047456A (en) * 1959-08-10 1962-07-31 Monsanto Chemicals Manufacture of paper products from fibers wet spun from polymer blends
US3058941A (en) * 1959-12-14 1962-10-16 Monsanto Chemicals Compositions comprising an organic polymer and an organo phosphorus compound

Also Published As

Publication number Publication date
NL287794A (en(2012)) 1900-01-01
GB1029944A (en) 1966-05-18
BE627201A (en(2012)) 1900-01-01
DK104605C (da) 1966-06-06
CH424459A (fr) 1966-11-15

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