US2132724A - Plasticizer and process of producing same - Google Patents

Plasticizer and process of producing same Download PDF

Info

Publication number
US2132724A
US2132724A US114927A US11492736A US2132724A US 2132724 A US2132724 A US 2132724A US 114927 A US114927 A US 114927A US 11492736 A US11492736 A US 11492736A US 2132724 A US2132724 A US 2132724A
Authority
US
United States
Prior art keywords
invert sugar
plasticizer
sugar
mannitol
sorbitol
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
US114927A
Inventor
Harold R Dalton
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.)
HAROLD R DALTON
JOHN S WARE
JOSEPH F LEETE
Original Assignee
HAROLD R DALTON
JOHN S WARE
JOSEPH F LEETE
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
Application filed by HAROLD R DALTON, JOHN S WARE, JOSEPH F LEETE filed Critical HAROLD R DALTON
Priority to US114927A priority Critical patent/US2132724A/en
Application granted granted Critical
Publication of US2132724A publication Critical patent/US2132724A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H17/00Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20Macromolecular organic compounds
    • D21H17/21Macromolecular organic compounds of natural origin; Derivatives thereof
    • D21H17/24Polysaccharides

Definitions

  • This invention relates to plasticizing agents of the saccharide type, and to the method of producing same.
  • One object of the invention is to produce a 5 plasticizing agent of this nature which is highly eflicient, inexpensive to manufacture and which produces permanent plasticizing efiects.
  • Another object of the invention is to produce such'a plasticizing agent which comprises a wa- IO ter solution of a saccharide or combination of saccharides and reduction products of these saccharides such as sorbitol mannitol, glycol, etc.
  • a further object] of the invention is the provision of a method of producing such a plasticiz- 5 ing agent which consists of partially reducing a water solution of invert sugar to the state wherein itis broken up into water, invert sugar, sorbitol, mannitol andother reduction products.
  • crystallization may be overcome by the addition of 20% to 30% of glycerine, by weight, to an invert sugar solution containing Ti invert sugar (dry weight).
  • Ethylene glycol in some cases is substituted for the glycerine.
  • the percentage may vary somewhat from the to ratio found necessary when glycerine is used.
  • partially reduced invert sugar plasticizer was readily and economically prepared by the two methods described be- 3 low:
  • the catalytic nickel was prepared from nickel formate reduced with hydrogen at 300 C.
  • the yield of reduced material was approximately 25%, consisting principally of sorbitol and mannitol.
  • ucts will be maintained in a stable plasticized state, and no tendency to become brittle will I have also found that in a plasticizer suitable for commercial use the ingredients may vary about as follows:
  • Invert sugar, glucose or fructose, etc. from a minimum of 50% to a maximum of water from a minimum of 10% to a maximum of 30% and reduced materials (mixture of sorbitol, mannitol and other reduced products) from 5% to 30%.
  • Partially reduced invert sugar plasticizer of a composition falling within the above range of compositions can be made by a slight variation of the method described.
  • glucose, fructose, xylose', sorbose, mannose, arabinose, etc. may be reduced by either of the methods described above and to the reduced product sufficlent invert sugar added to give a composition falling within the range specified.
  • a polysaccharide like cane sugar (sucrose) or molasses, may be used as a starting material, inversion and reduction being made to take place simultaneously.
  • the plasticizer may contain a small percentage of cane sugar.
  • sorbitol and mannitol which'will contain other reduction products, may be isolated from a reduced sugar mixture and added to an invert sugar solution to give a solution having a compositionfalling within the above mentioned range.
  • a highly satisfactory plasticizer made in accordance with my invention would comprise the following ingredients in about the proportions specified:
  • invert sugar I desire it understood that any mono-saccharide is to be included.
  • a plasticizer for paper and the like comprising a water solution of invert sugar, and the reaction products formed by. partially reducing a water solutionof invert sugar, said 'reaction products including sorbitol and mannitol the ratio by weight of the invert sugar to the reaction products being approximately as .2 is to 1, said reaction products serving to prevent crystallization of the unreduced sugar.
  • a plasticizer for paperand the like comprising a water solution of invert sugar, and the reaction products formed bypartially reducing a water solution of invert sugar, said reaction products including sorbitol and mannitol, the ratio by weight of the various ingredients being approximately as fo llowszinvert sugar 50 per. cent, reaction products 25 per cent, water 25 per cent.
  • reaction products including sorbitol and I mannitol, and said reaction products being in sufficient amount to prevent, crystallization of the unreduced sugar.

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented Oct. 11, 193
UNlT EDj- STATES 2,132,724 rms'rrorzaa AND PROCESS or rnonveme sum;
Harold R. Dalton, Teaneck, N. J., assignor to John S. Ware, New.York, N. Y., ilfosephll. mete,-
Chappaqua, N. Y., and
Application December 9, 1936, Serial No. 114,927
No Drawing.
4' Claims. (01. 91-68) This invention relates to plasticizing agents of the saccharide type, and to the method of producing same.
, One object of the invention is to produce a 5 plasticizing agent of this nature which is highly eflicient, inexpensive to manufacture and which produces permanent plasticizing efiects.
Another object of the invention is to produce such'a plasticizing agent which comprises a wa- IO ter solution of a saccharide or combination of saccharides and reduction products of these saccharides such as sorbitol mannitol, glycol, etc.
A further object] of the invention. isthe provision of a method of producing such a plasticiz- 5 ing agent which consists of partially reducing a water solution of invert sugar to the state wherein itis broken up into water, invert sugar, sorbitol, mannitol andother reduction products.
Other objects and advantages of my improved 20 plasticizing agent and the method of producing same will become more apparent as the description proceeds.
The disclosure made the basis of exemplifying the present inventivevconcept suggests a practical 25 embodiment thereof,'but the invention is notto be restricted to the exact, details of this disclosure, and the latter, therefore, is to be under- 1 stood from an illustrative, rather than a 'restrictive standpoint.
30 At the present time the'use of a water solution of invert sugar as a'plasticizer in the manufacture of paper, flexible glue and products such as gaskets and adhesives for gummed paper which I employ glue in their manufacture, does not give 35 altogether satisfactory results unless a small per- .centage of some other material is used along with it. The chief reason for this failure of water solutions of invert sugar to act as a satisfactory papergradually loses its flexibility and becomes brittle. Also paper which has had too much moisture removed from it during' drying on the paper machine, will come off the machine in a brittle condition as a result of the crystallization of the dextrose. In the case of glue products this crystallization proceeds at relative humidities as high as 65%. In a flexible glue the crystals very .55 quickly cover the surface of the material and gradually penetrate through the entire mass. -Here.agai n the crystallization is accompanied by increasing brittleness. In the case of glue products which vhave become brittle as a result of the crystallization of the dextrose, conditioning at high relative humidities has little effect in bringing them back to their original state.
The above mentioned crystallization may be overcome by the addition of 20% to 30% of glycerine, by weight, to an invert sugar solution containing Ti invert sugar (dry weight). Ethylene glycol in some cases is substituted for the glycerine. When using ethylene glycol, the percentage may vary somewhat from the to ratio found necessary when glycerine is used.
, Such additions, however, increase the cost of the product. 1,
Since water solutions of invert sugar are not satisfactory'in themselves for producing lasting and satisfactory plasticizing effects, I carried on 20 extensive investigations as to the best manner of treating such solutions so that they may be modified for satisfactory use as a plasticizer.
The aforementioned investigations resulted in the development of a partially reduced invert 25 sugar solution which gave highly satisfactory results when used as aplasticizer. This plasticizer, which will hereafter be termed partially reduced invert sugar plasticizer, was readily and economically prepared by the two methods described be- 3 low:
1. Reduction with sodium amalgam.--A water solution of invert sugar containing 76.0% invert sugar by weight was treated with 2 sodium amalgam. Equal weight of amalgam and invert sugar solution were used. The amalgam was added in small quantities. The reaction mixture was vigorously and continuously stirred until all of the amalgam was used up. The temperature of the mixture was maintained at 30 C. by plac- 40 ing the container in a water bath regulated to maintain this temperature. Sulphuric acid wasadded in small portions during the reaction in order to maintain the mixture neutral. The I yield of reduced material was approximately 7.0%. :1 i
- 2. Reduction with nickel in rm atmosphere of hydrogen.-A water solution of invert sugar .containing 77.0% invert sugar by weight was placed in an autoclave containing catalytic nickel. -The air was swept out of the chamber with hydrogen. The hydrogen pressure in the autoclave was finally.-raised 120.1500 lbs./sq. in. The mixture in the autoclave was stirred for four hours, the pressure of hydrogen being maintained at 1500 lbs./
occur.
sq. in. and the temperature at approximately 35 C.
- 'The catalytic nickel was prepared from nickel formate reduced with hydrogen at 300 C.
The yield of reduced material was approximately 25%, consisting principally of sorbitol and mannitol.
Other methods of reduction such as electrolytic and those employing zinc, magnesium, etc. can
ucts will be maintained in a stable plasticized state, and no tendency to become brittle will I have also found that in a plasticizer suitable for commercial use the ingredients may vary about as follows:
Invert sugar, glucose or fructose, etc., from a minimum of 50% to a maximum of water from a minimum of 10% to a maximum of 30% and reduced materials (mixture of sorbitol, mannitol and other reduced products) from 5% to 30%.
Partially reduced invert sugar plasticizer of a composition falling within the above range of compositions can be made by a slight variation of the method described. Thus glucose, fructose, xylose', sorbose, mannose, arabinose, etc., may be reduced by either of the methods described above and to the reduced product sufficlent invert sugar added to give a composition falling within the range specified.
A polysaccharide, like cane sugar (sucrose) or molasses, may be used as a starting material, inversion and reduction being made to take place simultaneously. In this method the plasticizer may contain a small percentage of cane sugar.
As a final method of preparation, sorbitol and mannitol, which'will contain other reduction products, may be isolated from a reduced sugar mixture and added to an invert sugar solution to give a solution having a compositionfalling within the above mentioned range.
A highly satisfactory plasticizer made in accordance with my invention would comprise the following ingredients in about the proportions specified:
Per cent Invert sugar .4... 50 Water 7 25 Reduced materials 25 It is also possible to produce-a satisfactory plasticizer by the addition of 25 lbs. of a mixture of commercial sorbitol and mannitol to 75 lbs. of invert sugar.
In producing sorbitol and mannitol commereially, it is possible that certain aforementioned reduction products may not be present in the commercial product, but I find that in my product these materials contribute greatly to the production of a more eflicient plasticizer.
,I have found that it is more economical to produce the sorbitol and mannitol directly in the invert sugar in about the proportions indicated, than to independently produce and refine each constituent and subsequently mix them.
I also find that a mixture such as mentioned above will make a more efficient plasticizer because it produces more stable and more lasting results when used as a plasticizer for paper, fabrics, glue and the like. This is particularly true when compared with the usual mixture of invert sugar and glycerine which is a common compound for such purposes.
Wherever in the specification and in the claims I have used the term invert sugar, I desire it understood that any mono-saccharide is to be included.
Having described my invention, what I claim as new and desire to secure by Letters Patent is:
1. A plasticizer for paper and the like comprising a water solution of invert sugar, and the reaction products formed by. partially reducing a water solutionof invert sugar, said 'reaction products including sorbitol and mannitol the ratio by weight of the invert sugar to the reaction products being approximately as .2 is to 1, said reaction products serving to prevent crystallization of the unreduced sugar.
2. A plasticizer for paperand the like comprising a water solution of invert sugar, and the reaction products formed bypartially reducing a water solution of invert sugar, said reaction products including sorbitol and mannitol, the ratio by weight of the various ingredients being approximately as fo llowszinvert sugar 50 per. cent, reaction products 25 per cent, water 25 per cent.
3. As a new article of manufacture, fibrous material impregnated and plasticized with a water solution of invert sugar in major proportion and the reaction products formed by partially reducing the water solution of invert sugar,
said reaction products including sorbitol and I mannitol, and said reaction products being in sufficient amount to prevent, crystallization of the unreduced sugar.
4. Asa new article of manufacture, paper impregnated with a water solution of invert sugar and the reaction products formed by partially hydrogenizing a water solution of invert sugar, ,said reaction products including sorbitol and HAROLD R. DALTON.
US114927A 1936-12-09 1936-12-09 Plasticizer and process of producing same Expired - Lifetime US2132724A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US114927A US2132724A (en) 1936-12-09 1936-12-09 Plasticizer and process of producing same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US114927A US2132724A (en) 1936-12-09 1936-12-09 Plasticizer and process of producing same

Publications (1)

Publication Number Publication Date
US2132724A true US2132724A (en) 1938-10-11

Family

ID=22358289

Family Applications (1)

Application Number Title Priority Date Filing Date
US114927A Expired - Lifetime US2132724A (en) 1936-12-09 1936-12-09 Plasticizer and process of producing same

Country Status (1)

Country Link
US (1) US2132724A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3243308A (en) * 1963-10-23 1966-03-29 Dept Of Agriculture And Inspec Amylosic films and method of making the same
US4481076A (en) * 1983-03-28 1984-11-06 International Telephone And Telegraph Corporation Redispersible microfibrillated cellulose
US4481077A (en) * 1983-03-28 1984-11-06 International Telephone And Telegraph Corporation Process for preparing microfibrillated cellulose
US5928473A (en) * 1997-01-15 1999-07-27 University Of Ottawa Inhibition of photo-yellowing in paper

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3243308A (en) * 1963-10-23 1966-03-29 Dept Of Agriculture And Inspec Amylosic films and method of making the same
US4481076A (en) * 1983-03-28 1984-11-06 International Telephone And Telegraph Corporation Redispersible microfibrillated cellulose
US4481077A (en) * 1983-03-28 1984-11-06 International Telephone And Telegraph Corporation Process for preparing microfibrillated cellulose
US5928473A (en) * 1997-01-15 1999-07-27 University Of Ottawa Inhibition of photo-yellowing in paper

Similar Documents

Publication Publication Date Title
US2627477A (en) Higher alkyl ketene dimer emulsion
US1863208A (en) Manufacture of ether derivatives of carbohydrates like cellulose
US2803558A (en) Method of treating adhesive gums
US2132724A (en) Plasticizer and process of producing same
US2184171A (en) Washing composition
US1522561A (en) Bleaching solution
US1319229A (en) Non-inflammable cellulose compound
US2483008A (en) Proofing proteinaceous fibers against biological attack
US3112214A (en) Process for sizing cellulose sheets with a starch derivative bearing vicinalglycol groups
US1502379A (en) Manufacture of cellulose derivatives
US1415850A (en) Alginate composition anb article
US2834777A (en) Methods of treating cellulose ethers
US2368660A (en) Composition of matter for flameproofing cellulosic media and method of making the same
US2553695A (en) Manufacture of cellulose ethers
US2110526A (en) Method for the preparation of cellulose ethers
US2067853A (en) Method for the preparation of aralkyl ethers of cellulose
US1938360A (en) Manufacture of alkyl ethers of cellulose
GB224891A (en) Improved dentifrice material
US2831853A (en) Manufacture of sizing
US2105310A (en) Agglutinant
US2159376A (en) Making of low viscosity cellulose ethers
US1858018A (en) Process for the manufacture of ethers of carbohydrates
US2260343A (en) Gelatinized nitrocellulose and method of making same
US3313803A (en) Hydroxyalkyl starch ether products
US1864546A (en) Process of preparing cellulose ethers