GB783745A - Production of cellular cured polymeric material - Google Patents

Production of cellular cured polymeric material

Info

Publication number
GB783745A
GB783745A GB35105/55A GB3510555A GB783745A GB 783745 A GB783745 A GB 783745A GB 35105/55 A GB35105/55 A GB 35105/55A GB 3510555 A GB3510555 A GB 3510555A GB 783745 A GB783745 A GB 783745A
Authority
GB
United Kingdom
Prior art keywords
methyl
radical
para
benzenesulphonyl
phenyltriazene
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
Application number
GB35105/55A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid 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
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB783745A publication Critical patent/GB783745A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/06Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
    • C08J9/10Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing nitrogen, the blowing agent being a compound containing a nitrogen-to-nitrogen bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cellular cured polymeric material, e.g. of rubber or of urea, phenol, or melamine aldehyde resin, or of a vinyl polymer is prepared by incorporating into a mix of the uncured material as a blowing agent an organic N-substituted sulphonyltriazene, and heating to expand and cure the mix. The N-substituted sulphonyltriazene may have the formula <FORM:0783745/IV (a)/1> in which R is a cycloalkyl, aralkyl, aryl or heterocyclic radical, R1 is an aryl or heterocyclic radical, and R2 is an aliphatic radical linked through a saturated carbon atom to the nitrogen, or the formula <FORM:0783745/IV (a)/2> in which R is a mono- or di-arylene radical in which the nuclei of the diarylene radical may be interposed by an oxygen or sulphur atom, R1 is an aromatic or heterocyclic radical, and R2 is an aliphatic radical linked through a saturated carbon atom to the nitrogen, or the formula <FORM:0783745/IV (a)/3> in which R is a cycloalkyl, aralkyl, aryl, or heterocyclic radical, R1 is a diarylene radical in which the nuclei may be interposed by an oxygen or sulphur atom, and R2 is an aliphatic radical linked through a saturated carbon atom to the nitrogen. Several compounds of the above formul are specified. In Example 3 a cellular material was prepared by heating at 153 DEG C. for 40 minutes and 500 p.s.i., and at 100 DEG C. for 60 minutes, a mixture of 100 parts (by weight) of a vinyl resin, 130 parts dioctyl phthalate, a heat stabilizer (4 pts.) and 10 parts of 1 - benzenesulphonyl - 3 - methyl - 3 - phenyltriazene. Other triazene blowing agents are specified.ALSO:An N-substituted sulphonyltriazene for use as a blowing agent in preparing cellular cured polymeric material (see Group V) may have the formula <FORM:0783745/IV (a)/1> in which R is a cycloalkyl, aralkyl, aryl or heterocyclic radical, R1 is an aryl or heterocyclic radical, and R2 is an aliphatic radical linked through a saturated carbon atom to the nitrogen, or the formula <FORM:0783745/IV (a)/2> in which R is a mono- or diarylene radical in which the nuclei of the diarylene radical may be interposed by an oxygen or sulphur atom, R1 is an aromatic or heterocyclic radical, and R2 is an aliphatic radical linked through a saturated carbon atom to the nitrogen, or the formula <FORM:0783745/IV (a)/3> in which R is a cycloalkyl, aralkyl, aryl, or heterocyclic radical, R1 is a diarylene radical in which the nuclei may be interposed by an oxygen or sulphur atom, and R2 is an aliphatic radical linked through a saturated carbon atom to the nitrogen. The N-substituted sulphonyltriazene may be prepared by treatment of a monosulphonamide, e.g. cyclohexane sulphonamide, with a diazonium salt, e.g. benzene diazonium chloride, to obtain a diazosulphonamide. The latter is then treated with, for example, dimethyl or diethyl sulphate or with acrylonitrile to obtain the aliphatic radical R2. Alternatively a bis-sulphonamide, e.g. pxylene disulphonamide, or a tetrazo compound, e.g. a salt of 4,41-diamino-diphenyl ether, may be analogously rested to form bis-sulphonyltriazenes. Lists of starting materials given include compounds substituted with alkyl, alkoxy, acetoxy, acidylamino, chlorine, cyano and nitro radicals. Specified products are 1-benzenesulphonyl-3-methyl-3-phenyltriazene, 1-benzenesulphonyl - 3 - methyl - 3 - para - tolyltriazene, 1 - benzenesulphonyl - 3 - methyl - 3 - ortho-tolyltriazene, 1 - benzenesulphonyl - 3 - methyl-3 - para - anisyltriazene, 1 - benzenesulphonyl-3 - methyl - 3 - para - chlorophenyltriazene, 1 - benzenesulphonyl - 3 - methyl - 3 - meta-chlorophenyltriazene, 1 - benzenesulphonyl - 3 - ethyl - 3 - para - tolyltriazene, 1 - benzenesulphonyl - 3 - cyanoethyl - 3 - phenyltriazene, 1 - benzenesulphonyl - 3 - cyanoethyl - 3 - para-chlorophenyltriazene, 1 - benzenesulphonyl - 3 - cyanoethyl - 3 - para - tolyltriazene, 1 - phenylmethanesulphonyl - 3 - methyl - 3 - meta-tolyltriazene, 1 - benzylsulphonyl - 3 - methyl-3 - phenyltriazene, 1 - (para - toluenesulphonyl)-3 - methyl - 3 - phenyltriazene, 1 - (para-toluenesulphonyl) - 3 - methyl - 3 - para - tolyltriazene, 1 - (para - toluenesulphonyl) - 3 - cyanoethyl - 3 - phenyltriazene, 1 - (para) - methoxybenzenesulphonyl) - 3 - ethyl - 3 - (para-methylphenyl) - triazene, 1 - (para - methoxybenzenesulphonyl) - 3 - methyl - 3 - phenyltriazene, 1 - (ortho - chlorobenzenesulphonyl)-3 - cyanoethyl - 3 - phenyltriazene, 1 - (para-chlorobenzenesulphonyl) - 3 - methyl - 3 - phenyltriazene, 1 - (5 - acetamido - 2 - thiadiazolesulphonyl) - 3 - methyl - 3 - para - tolyltriazene, 1 - (5 - quinolinesulphonyl) - 3 - cyanoethyl - 3 - para - anisyltriazene, 3:31 - (4:41-biphenyl) - bis - (3 - methyl - 1 - benzenesulphonyltriazene) and 1:11 - (1:5 - naphtholenedisulphonyl) - bis - (3 - methyl - 3 - phenyltriazine. The above triazenes are numbered: <FORM:0783745/IV (a)/4>ALSO:Cellular cured, polymeric material, e.g. of rubber or of urea, phenol, or melamine aldehyde resin, or of a vinyl polymer is prepared by incorporating into a mix of the uncured material as a blowing agent an organic N-substituted sulphonyltriazine, and heating to expand and cure the mix. The N-substituted sulphonyltriazene may have the formula: <FORM:0783745/V/1> in which R is a cycloalkyl, aralkyl, aryl or heterocyclic radical, R1 is an aryl or heterocyclic radical, and R2 is an aliphatic radical linked through a saturated carbon atom to the nitrogen, or the formula: <FORM:0783745/V/2> in which R is a mono- or diarylene radical in which the nuclei of the diarylene radical may be interposed by an oxygen or sulphur atom, R1 is an aromatic or heterocyclic radical and R2 is an aliphatic radical linked through a saturated carbon atom to the nitrogen, or the formula: <FORM:0783745/V/3> in which R is a cycloalkyl, aralkyl, aryl, or heterocyclic radical, R1 is a diarylene radical in which the nuclei may be interposed by an oxygen or sulphur atom, and R2 is an aliphatic radical linked through a saturated carbon atom to the nitrogen. The N-substituted sulphonyltriazene may be prepared by treatment of a monosulphonamide, e.g. cyclohexane sulphonamide, with a diazonium salt, e.g. benzene diazonium chloride, to obtain a diazosulphonamide. The latter is then treated with, for example, dimethyl or diethyl sulphate or with acrylonitrile to obtain the aliphatic radical R2. Alternatively a bis-sulphonamide, e.g. p-xylene disulphonamide, or a tetrazo compound, e.g. a salt of 4, 41 diamino-diphenyl ether, may be treated with the diazonium salt. Several compounds of the above formulae are specified. In one Example samples of cellular material are prepared by heating at 153 DEG C. for 35 minutes, and at 130 DEG C. for 60 minutes, mixes comprising 100 parts by weight of plasticized rubber, vulcanizing and other ingredients, and 1,5 parts of a blowing agent. Various samples are prepared using several different blowing agents including 1-benzenesulphonyl-3-methyl-3-phenyl-triazene, 3, 31-(4, 41 biphenyl)-bis-[3 methyl-1-benzene-sulphonyltriazene], 1, 11 (1, 51 naphthalene disulphonyl)-bis-[3-methyl-3 phenyl-triazene].
GB35105/55A 1954-12-14 1955-12-07 Production of cellular cured polymeric material Expired GB783745A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US783745XA 1954-12-14 1954-12-14

Publications (1)

Publication Number Publication Date
GB783745A true GB783745A (en) 1957-09-25

Family

ID=22143636

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35105/55A Expired GB783745A (en) 1954-12-14 1955-12-07 Production of cellular cured polymeric material

Country Status (1)

Country Link
GB (1) GB783745A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7134572B2 (en) 2001-10-03 2006-11-14 Sca Hygiene Products Gmbh Container for a stack of interfolded tissue sheets
CN116218097A (en) * 2022-09-07 2023-06-06 海啊科技股份有限公司 PVC material capable of controlling temperature to foam and preparation method and application thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7134572B2 (en) 2001-10-03 2006-11-14 Sca Hygiene Products Gmbh Container for a stack of interfolded tissue sheets
CN116218097A (en) * 2022-09-07 2023-06-06 海啊科技股份有限公司 PVC material capable of controlling temperature to foam and preparation method and application thereof
CN116218097B (en) * 2022-09-07 2024-05-24 海啊科技股份有限公司 PVC material capable of controlling temperature to foam and preparation method and application thereof

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