US2614940A - Ultraviolet light absorbing film - Google Patents

Ultraviolet light absorbing film Download PDF

Info

Publication number
US2614940A
US2614940A US68624A US6862448A US2614940A US 2614940 A US2614940 A US 2614940A US 68624 A US68624 A US 68624A US 6862448 A US6862448 A US 6862448A US 2614940 A US2614940 A US 2614940A
Authority
US
United States
Prior art keywords
film
ultraviolet light
light absorbing
absorbing film
salt
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
US68624A
Other languages
English (en)
Inventor
Harlan B Freyermuth
William O Ney
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.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
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 General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US68624A priority Critical patent/US2614940A/en
Priority to FR1002886D priority patent/FR1002886A/fr
Priority to DEG694A priority patent/DE860271C/de
Priority to BE492985A priority patent/BE492985A/fr
Priority to GB33132/49A priority patent/GB671857A/en
Priority to CH289699D priority patent/CH289699A/fr
Application granted granted Critical
Publication of US2614940A publication Critical patent/US2614940A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
    • G03C1/8155—Organic compounds therefor

Definitions

  • This invention relates to ultraviolet light absorbing films. 7
  • plastic materials of both the water-soluble and water insoluble type such as gelatin, polyvinyl alcohol, cellulose acetate and the like become colored, usually yellowing, and sometimes brittle and many eventually deteriorate upon exposure to sunlight.
  • the present invention is concerned with ultraviolet light absorbers for the water soluble film forming materials which may be used themselves in packaging, as for example cellophane, or which may be used as a coating upon other materials which fade or deteriorate insunlight.
  • the absorption of ultraviolet light in materials such as cellophane is particularlyimportant because of the wide spread usesof cellophane as a packaging material, allowing fading or deterioration of the goods which the package contains.
  • the absorber should be capable of absorbing substantially all of; the ultraviolet light within the Wave length range 200 to 400 millimicrons and even into'the visible range as high as 4.40 millimicrons.
  • a film is cast from a water solution of a water soluble film forming plastic containing a compound having the following general structure:
  • one B is hydrogen and the other R is an alkaline sulphonate radical.
  • the sulphonic acid is neutralized with any of various alkaline material including alkaline earth metals, ammonia, amines such as aliphatic, aromatic, cycloparafiinic and heterooyclic amines, and preferable alkali metals, alkali hydroxides,10r alkaline alkali metal salts (e. g. NazCOal.
  • alkaline earth metals ammonia
  • amines such as aliphatic, aromatic, cycloparafiinic and heterooyclic amines
  • alkali metals alkali hydroxides,10r alkaline alkali metal salts (e. g. NazCOal.
  • alkali hydroxides alkali hydroxides
  • 10r alkaline alkali metal salts e. g. NazCOal.
  • 'It is an important element of the present in;- vention that the compound have a pH in the range of 5 to 9.5.
  • the above compound, for example, in acid form has a pH of about 1.5
  • Example 2 Ten parts of the sulphonic acid product of Example 1 was dissolved by heating in parts like.
  • Example 1 To 90 parts of a 10% aqueoussolution of gela-'- tin was added 1.0 part of the sodium' salt of 2,4-dihydroxybenzophenone-5-su1fonic acid. AA film resembling thatthe Example 1 was obtained.
  • the film of' the present invention may be a self-supported film such as the cellophane used in packaging or it may be used as a protective coating on other bases such as water soluble or water insoluble plastic materialsas, for example, photographic cellulose acetate film, glass or the
  • the compounds of the present invention are cclorlessandj s such absorb very little visible .lig ht-and subsequently do not distort thecolor balance of articles which they may protect. They are useful in photographic .filters sun tan lotions, vand cellophane potato chippackages, .among other uses. 3 Y
  • the compound ofExample 1 contains :the sul- -Ionic acid group in the substituted :tresorcinol) ring-because onloxidation, benzoic .acid is isolated from the reaction products, which demonstrates that sulfonation doe-snot take place in the other ring.
  • Examples of “film-forming "organic plastic mater-ials which are soluble in the aqueousmed'iums "hereinemp'loyed,-that is aqueous mediums h-aving -a pH in the range-o-f 5 to 9;5 include regencellulose,- partially hydrolyzed polyvinyl "acetate, polyvinyl alcohol, elatin, carboxymethyl' cellulose, hydroxyxn'thyl cellulose, urea-formaldehy'de resins, melamine iormaldhyde resins,
  • the material absorbs substantially all of the light below :the visual range whileritself being colorless .or veryipale yellow.
  • An 'improvedultraviolet light absorbing film comprising a film-forming plastic soluble in an aqueous medium having a pH of 5 to 9.5 and a salt :of a .sul-fonic :acid, which sulfonic acid has the formula: v

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Mechanical Engineering (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
US68624A 1948-12-31 1948-12-31 Ultraviolet light absorbing film Expired - Lifetime US2614940A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US68624A US2614940A (en) 1948-12-31 1948-12-31 Ultraviolet light absorbing film
FR1002886D FR1002886A (fr) 1948-12-31 1949-12-20 Pellicule absorbant la lumière ultra-violette
DEG694A DE860271C (de) 1948-12-31 1949-12-27 Verfahren zur Herstellung von ultraviolettes Licht absorbierenden Filmen
BE492985A BE492985A (fr) 1948-12-31 1949-12-28 Pellicule absorbant la lumière ultra-violette
GB33132/49A GB671857A (en) 1948-12-31 1949-12-28 Ultraviolet light absorbing film
CH289699D CH289699A (fr) 1948-12-31 1949-12-31 Solution destinée à la formation de pellicules absorbant la lumière ultra-violette et procédé pour la préparation de cette solution.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US68624A US2614940A (en) 1948-12-31 1948-12-31 Ultraviolet light absorbing film

Publications (1)

Publication Number Publication Date
US2614940A true US2614940A (en) 1952-10-21

Family

ID=22083716

Family Applications (1)

Application Number Title Priority Date Filing Date
US68624A Expired - Lifetime US2614940A (en) 1948-12-31 1948-12-31 Ultraviolet light absorbing film

Country Status (6)

Country Link
US (1) US2614940A (fr)
BE (1) BE492985A (fr)
CH (1) CH289699A (fr)
DE (1) DE860271C (fr)
FR (1) FR1002886A (fr)
GB (1) GB671857A (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2748021A (en) * 1953-06-24 1956-05-29 Eastman Kodak Co Solubilized benzal derivatives of alpha-methyl-alpha-phenyl hydrazines and ultraviolet radiation absorbing products thereof
DE1002625B (de) * 1952-10-31 1957-02-14 Eastman Kodak Co Gegen Einwirkung der Ultraviolettstrahlung geschuetztes photographisches Material
DE958526C (de) * 1952-10-31 1957-02-21 Eastman Kodak Co Gegen Einwirkung von Ultraviolett-Strahlung geschuetztes photographisches Material mit einer Ultraviolett absorbierenden Schicht
DE964654C (de) * 1952-10-31 1957-05-23 Eastman Kodak Co Photographisches Material mit einer ultraviolettabsorbierenden Schicht
US2876210A (en) * 1954-02-10 1959-03-03 Gen Aniline & Film Corp 2,2'-dihydroxy-4, 4'-substituted benzophenones as ultraviolet absorbents for gr-a rubber
US2888315A (en) * 1956-01-24 1959-05-26 Joseph E Moore Process for preventing yellowing of wool
US2944912A (en) * 1958-07-31 1960-07-12 Printing Arts Res Lab Inc Ultraviolet absorbing watercolor paint compositions
US2983604A (en) * 1955-11-03 1961-05-09 Gen Aniline & Film Corp Quenching solution for fluorescent photographic paper employed in the manufacture ofhalftone negatives
US2989416A (en) * 1958-01-06 1961-06-20 Du Pont Werner complexes of orthohydroxyl substituted benzophenone
US3043709A (en) * 1957-08-01 1962-07-10 Du Pont Organic polymeric structure having an ultraviolet light absorbent compound incorporated therein
US3076723A (en) * 1958-05-26 1963-02-05 Du Pont Coating weight determination by means of ultraviolet light
US3124584A (en) * 1964-03-10 Process for the production of hetero-
US3160665A (en) * 1957-03-06 1964-12-08 Ciba Ltd Hydroxy-benzophenones
US3214463A (en) * 1960-05-12 1965-10-26 Du Pont Uv-absorbing sulfonated benzophenone derivatives
US3247127A (en) * 1960-04-14 1966-04-19 Eastman Kodak Co Light-absorbing water-permeable colloid layer containing an oxonol dye
US3506758A (en) * 1964-03-10 1970-04-14 Colgate Palmolive Co Substantive sunscreening compositions
US3670074A (en) * 1971-01-22 1972-06-13 Cyril Doner Sunscreen formulation containing triethanolamine neutralized 2-hydroxy-4-methoxy-benzophenone-5-sulfonic acid
US3867302A (en) * 1971-12-24 1975-02-18 Sinloihi Co Ltd Organic phosphors and process for production thereof
US4840788A (en) * 1986-07-15 1989-06-20 Ici Americas Inc. Nonalcoholic sunscreen gel

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU87142A1 (fr) * 1988-02-25 1989-09-20 Oreal Societe Anonyme Francais Composition cosmetique pour le maintien de la coiffure contenant un polymere d'oxazoline et un acide 2-hydroxy 4-methoxy benzophenone 5-sulfonique salifie ou non
US5275810A (en) * 1988-02-25 1994-01-04 L'oreal Cosmetic composition for maintaining the hairstyle containing an oxazoline polymer and a 2-hydroxy-4-methoxy-benzophenone-5-sulphonic acid, salified or otherwise

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2069773A (en) * 1934-09-15 1937-02-09 Du Pont Delustered cellulosic product and method of preparing same
US2099441A (en) * 1934-09-15 1937-11-16 Du Pont Cellulosic product and method for preparing same
US2199927A (en) * 1937-03-17 1940-05-07 Du Pont Cellulosic pellicle
US2434496A (en) * 1945-03-02 1948-01-13 Dow Chemical Co Light stable compositions comprising polymeric vinylidene chloride or vinyl chloride and certain 5-substituted 2-hydroxybenzophenones

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE640908C (de) * 1933-03-12 1937-01-15 I G Farbenindustrie Akt Ges Farblose oder schwach gefaerbte Schutzhuelle fuer licht- oder luftempfindliche Waren aller Art

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2069773A (en) * 1934-09-15 1937-02-09 Du Pont Delustered cellulosic product and method of preparing same
US2099441A (en) * 1934-09-15 1937-11-16 Du Pont Cellulosic product and method for preparing same
US2199927A (en) * 1937-03-17 1940-05-07 Du Pont Cellulosic pellicle
US2434496A (en) * 1945-03-02 1948-01-13 Dow Chemical Co Light stable compositions comprising polymeric vinylidene chloride or vinyl chloride and certain 5-substituted 2-hydroxybenzophenones

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3124584A (en) * 1964-03-10 Process for the production of hetero-
DE1002625B (de) * 1952-10-31 1957-02-14 Eastman Kodak Co Gegen Einwirkung der Ultraviolettstrahlung geschuetztes photographisches Material
DE958526C (de) * 1952-10-31 1957-02-21 Eastman Kodak Co Gegen Einwirkung von Ultraviolett-Strahlung geschuetztes photographisches Material mit einer Ultraviolett absorbierenden Schicht
DE964654C (de) * 1952-10-31 1957-05-23 Eastman Kodak Co Photographisches Material mit einer ultraviolettabsorbierenden Schicht
DE969374C (de) * 1952-10-31 1958-05-22 Eastman Kodak Co Gegen Einwirkung der ultravioletten Strahlung geschuetztes photographisches Material mit einer Ultraviolett absorbierenden Schicht
US2748021A (en) * 1953-06-24 1956-05-29 Eastman Kodak Co Solubilized benzal derivatives of alpha-methyl-alpha-phenyl hydrazines and ultraviolet radiation absorbing products thereof
US2876210A (en) * 1954-02-10 1959-03-03 Gen Aniline & Film Corp 2,2'-dihydroxy-4, 4'-substituted benzophenones as ultraviolet absorbents for gr-a rubber
US2983604A (en) * 1955-11-03 1961-05-09 Gen Aniline & Film Corp Quenching solution for fluorescent photographic paper employed in the manufacture ofhalftone negatives
US2888315A (en) * 1956-01-24 1959-05-26 Joseph E Moore Process for preventing yellowing of wool
US3160665A (en) * 1957-03-06 1964-12-08 Ciba Ltd Hydroxy-benzophenones
US3043709A (en) * 1957-08-01 1962-07-10 Du Pont Organic polymeric structure having an ultraviolet light absorbent compound incorporated therein
US2989416A (en) * 1958-01-06 1961-06-20 Du Pont Werner complexes of orthohydroxyl substituted benzophenone
US3076723A (en) * 1958-05-26 1963-02-05 Du Pont Coating weight determination by means of ultraviolet light
US2944912A (en) * 1958-07-31 1960-07-12 Printing Arts Res Lab Inc Ultraviolet absorbing watercolor paint compositions
US3247127A (en) * 1960-04-14 1966-04-19 Eastman Kodak Co Light-absorbing water-permeable colloid layer containing an oxonol dye
US3214463A (en) * 1960-05-12 1965-10-26 Du Pont Uv-absorbing sulfonated benzophenone derivatives
US3506758A (en) * 1964-03-10 1970-04-14 Colgate Palmolive Co Substantive sunscreening compositions
US3670074A (en) * 1971-01-22 1972-06-13 Cyril Doner Sunscreen formulation containing triethanolamine neutralized 2-hydroxy-4-methoxy-benzophenone-5-sulfonic acid
US3867302A (en) * 1971-12-24 1975-02-18 Sinloihi Co Ltd Organic phosphors and process for production thereof
US4840788A (en) * 1986-07-15 1989-06-20 Ici Americas Inc. Nonalcoholic sunscreen gel

Also Published As

Publication number Publication date
GB671857A (en) 1952-05-14
FR1002886A (fr) 1952-03-11
CH289699A (fr) 1953-03-31
DE860271C (de) 1952-12-18
BE492985A (fr) 1950-01-14

Similar Documents

Publication Publication Date Title
US2614940A (en) Ultraviolet light absorbing film
US2704710A (en) Precipitation of azo dyes in silver halide emulsions by means of guanidine and biguanide compounds containing long alkyl chains
US2693492A (en) - dihydroxy -
US2710274A (en) Multi-layer glass sheet
US3215530A (en) Color photographic element protected against fading and method of applying protective film thereto
US3754919A (en) Photographic layers which contain uvabsorbers
US3772072A (en) Method for treating reverse osmosis membranes
Wettermark et al. Transient species in the photolysis of anils
GB495479A (en) Improvements in protective casings for goods sensitive to light and air
US3471293A (en) Antihalation and filter dyes for photographic materials
US3591575A (en) Preparation of diazonium compounds
DK124203B (da) Analogifremgangsmåde til fremstilling af 1,2,3,11b-tetrahydropyrido[3,4,5:m,n]thioxanthener eller syreadditionssalte deraf.
US2440070A (en) Optical filter and method of manufacture
DK138418B (da) Analogifremgangsmåde til fremstilling af 3-hydroxy-alfa-(1-aminoethyl)-benzylalkohol-derivater eller syreadditionssalte deraf.
JPS5837078A (ja) フオトクロミツク感光性組成物
JPS61138687A (ja) フオトクロミツク感光性組成物
GB1286885A (en) Process for preparing fluorane compounds
US2388816A (en) Photographic developer
DE1002625B (de) Gegen Einwirkung der Ultraviolettstrahlung geschuetztes photographisches Material
ES353818A1 (es) Un procedimiento para la produccion de una forma cristalinatermoestable de un derivado de bis-triacinilamino-estilbeno.
US2748021A (en) Solubilized benzal derivatives of alpha-methyl-alpha-phenyl hydrazines and ultraviolet radiation absorbing products thereof
US2829149A (en) New fuchsine cyanide
US3740229A (en) Diazotype photographic copying material for heat development
US2798067A (en) 2-imino-4-thiazolidones and preparation
US2122828A (en) Light filter