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1. 发明授权

US4058491A Cationic hydrogels based on heterocyclic N-vinyl monomers 失效
公开(公告)号：US4058491A
公开(公告)日：1977-11-15
申请号：US549097
申请日：1975-02-11
申请人： Robert Steckler
发明人： Robert Steckler
IPC分类号： C08F220/34 , C08F226/06 , C08F220/20 , C08F26/00
CPC分类号： C08F226/06 , C08F220/34 , Y10S514/944
摘要： Novel cationic hydrogels, containing basic (cationic) groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are stable, three-dimensional polymer networks, having good water permeability and mechanical properties. They are obtained by simultaneous polymerization and cross-linking in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) a heterocyclic monomer preferably an N-vinyl lactam, (b) a cationic monomer -- usually an ester of acrylic or methacrylic acid with an amino alcohol, the terminal amino group of which may be quaternized, such as dimethylaminoethyl methacrylate or acrylate and the quaternized derivatives thereof, and (c) a cross-linking agent, such as a glycol or polyglycol diacrylate or dimethacrylate and also, preferably, (d) at least one acrylic monomer capable of polymerizing to a very high molecular weight, such as hydroxyethyl- or hydroxypropyl-acrylate or methacrylate, or a lower alkyl acrylate or methacrylate; if desired there may also be present in the monomer mixture (e) other polymerizable ethylenically unsaturated monomers, which are copolymerizable with components (a), (b), (c) and (d). The thus obtained cationic hydrogels are useful for combining by reaction or complexing, with water soluble or dispersible materials having an opposite charge; such as acidic or anionic agricultural chemicals (insecticides, herbicides, fungicides, plant growth regulators, etc.), germicides, pharmaceuticals, cosmetics, hormones, enzymes, flavors, fragrances, antiperspirants, metals and the like, both to recover such acidic or anionic materials from an aqueous medium and for purifying water containing them, and also for the preparation of a complex or other combination of the cationic hydrogel with such anionic materials which may be useful per se or from which the complexed or combined acidic or anionic material may be slowly or controllably released.

2. 发明授权

US4009201A Polymerizable cationic monomers 失效
标题翻译：可聚合的阳离子单体
公开(公告)号：US4009201A
公开(公告)日：1977-02-22
申请号：US471441
申请日：1974-05-20
申请人： Robert Steckler , Seymour Martin Linder
发明人： Robert Steckler , Seymour Martin Linder
IPC分类号： C08F20/34 , C07C69/54
CPC分类号： C08F20/34
摘要： Novel polymerizable cationic monomers, which contain two or more cationic groups in the molecule, and homopolymers and copolymers thereof are described. These novel cationic monomers are compounds represented by the general formula: ##STR1## AND THE QUATERNIZED DERIVATIVES THEREOF (IN WHICH THE TERMINAL TERTIARY AMINO GROUP HAS BEEN QUATERNIZED TO A QUATERNARY AMMONIUM GROUP) OF THE FORMULA: ##STR2## In the forgoing Formulas 1 and 2: A, each of which may be the same or different, represents an alkylene group of from 1 to about 20 carbon atoms but including oxygen interrupted alkylene groups (i.e.; a polyglycol ether group of the formula ##STR3## WHEREIN R.sup.5 represents H, methyl or ethyl and x represents an integer of from 1 to about 20);R represents H or methyl;R.sup.1 represents H or, when R is H, an alkyl group of 1 to 4 carbon atoms, R.sup.1 preferably H or methyl;R.sup.2, r.sup.3 and R.sup.4, each of which may be the same or different, each represents alkyl of from 1 to about 20 carbon atoms, aryl (preferably phenyl), alkaryl (preferably benzyl) or the R.sup.2 and R.sup.3, on the same nitrogen atom, taken together may represent a divalent aliphatic group of 4 to 5 atoms which jointly with the amino nitrogen forms a five or six membered heterocyclic amino group such as pyrrolidinyl, piperidinyl, morpholino or thiamorpholino and these groups may have a lower alkyl substituent such as a methyl or ethyl group:X and Y, each of which may be the same or different, each represents an anion (forming the anionic portion of a quaternary ammonium group) such as a halogen ion (fluorine, chlorine, bromine or iodine), a sulfate ion, a hydroxyl ion or a nitrate ion, X is preferably chlorine or bromine and Y is preferably chlorine, bromine or lower alkyl sulfate (i.e.; methyl or ethyl sulfate), and in case there are two or more X's in the molecule each of them may be the same or different;n represents an integer, including 0, of from 0 to about 10; andm represents an integer of from 1 to about 5.These polymerizable cationic monomers are of primary interest for the production of polymers and more particularly copolymers (with such co-monomers as styrene, vinyl acetate, vinyl chloride, acrylic esters, acrylamide and acrylonitrile) but including homopolymers, especially in the case of compounds in which the acyl group is that of acrylic acid or methacrylic acid, having cationic properties with resultant improvement in such properties as adhesion, anti-static properties, dye receptivity, etc.
摘要翻译：描述了在分子中含有两个或更多个阳离子基团的新型可聚合阳离子单体及其均聚物和共聚物。这些新型阳离子单体是由以下通式表示的化合物：

3. 发明授权

US4163092A Cationic hydrogels based on hydroxyalkyl acrylates and methacrylates 失效
公开(公告)号：US4163092A
公开(公告)日：1979-07-31
申请号：US825521
申请日：1977-08-18
申请人： Robert Steckler
发明人： Robert Steckler
IPC分类号： C08F220/28 , C08F220/34 , C08F220/36 , C08F220/06
CPC分类号： C08F220/28 , C08F220/34 , C08F220/36 , Y10S514/944
摘要： Novel cationic hydrogels, containing basic (cationic) groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are three-dimensional polymer networks, having good water permeability and mechanical properties, and are obtained by simultaneous polymerization and crosslinking, in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) hydroxyalkyl acrylate or methacrylate, (b) a cationic monomer -- usually an ester of acrylic or methacrylic acid with an amino alcohol, the terminal amino group of which may be quaternized, such as dimethylaminoethyl methacrylate or acrylate and the quaternized derivatives thereof, and (c) a cross-linking agent, such as glycol diacrylate or dimethacrylate; if desired there may also be present (d) one or more additional monomers, usually an acrylic monomer such as an alkyl acrylate or methacrylate, acrylamides etc. (although other monomers such as vinyl acetate, styrene, etc. may also be used) which is copolymerizable with (a), (b) and (c). The thus obtained cationic hydrogels are useful for combining, by reaction or complexing, with materials having an opposite charge; such as acidic or anionic agricultural chemicals (insecticides, herbicides, fungicides, plant growth regulators, etc.), germicides, pharmaceuticals, cosmetics, hormones, enzymes, flavors, fragrances, antiperspirants, metals and the like, both to recover such acidic or anionic materials from an aqueous medium and for purifying water containing them, and also for the preparation of a complex or other combination of the cationic hydrogel with such materials which may be useful per se or from which the complexed or combined acidic or anionic material may be slowly or controllably released.

4. 发明授权

US4036788A Anionic hydrogels based on heterocyclic N-vinyl monomers 失效
公开(公告)号：US4036788A
公开(公告)日：1977-07-19
申请号：US549095
申请日：1975-02-11
申请人： Robert Steckler
发明人： Robert Steckler
IPC分类号： A01N25/10 , A61K8/04 , A61K8/81 , A61K47/48 , A61L9/04 , A61Q19/00 , C08F220/20 , C08F226/06
CPC分类号： A61K8/8182 , A01N25/10 , A61K47/48184 , A61K8/042 , A61L9/048 , A61Q19/00 , C08F226/06 , Y10S514/944
摘要： Novel anionic hydrogels, containing acidic groups, and their preparation are described. These novel hydrogels are stable, three-dimensional polymer networks, having good water permeability and mechanical properties. They are obtained by simultaneous polymerization and cross-linking, in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) a heterocyclic monomer preferably an N-vinyl lactam, (b) a polymerizable acidic monomer, such as acrylic or methacrylic acid, sulfo-ethyl methacrylate or a sulfated or phosphated derivative of a hydroxyalkyl- acrylate or methacrylate and (c) a cross-linking agent, such as a glycol or polyglycol diacrylate or dimethacrylate and also, preferably, (d) at least one acrylic monomer capable of polymerizing to a very molecular weight, such as hydroxyethyl- or hydroxypropyl-acrylate or methacrylate, acrylamide or methacrylamide, or a lower alkyl acrylate or methacrylate; if desired there may also be present in the monomer mixture (e) other polymerizable ethylenically unsaturated monomers, which are copolymerizable with components (a), (b), (c) and (d). The thus obtained anionic hydrogels are useful for combining by reaction or complexing, with water soluble or dispersible materials having an opposite charge; such as basic or cationic agricultural chemicals (insecticides, herbicides, fungicides, plant growth regulators, etc.), germicides, pharmaceuticals, cosmetics, hormones, enzymes, flavors, fragrances, antiperspirants, metals and the like, both to recover such basic or cationic materials from an aqueous medium and for purifying water containing them, and also for the preparation of a complex or other combination of the anionic hydrogel with such materials which may be useful per se or from which the complexed or combined basic or cationic material may be slowly or controllably released.

5. 发明授权

US4060678A Cationic hydrogels based on hydroxyalkyl acrylates and methacrylates 失效
公开(公告)号：US4060678A
公开(公告)日：1977-11-29
申请号：US549096
申请日：1975-02-11
申请人： Robert Steckler
发明人： Robert Steckler
IPC分类号： C08F220/28 , C08F220/34 , C08F220/36 , C08F220/06
CPC分类号： C08F220/28 , C08F220/34 , C08F220/36 , Y10S514/944
摘要： Novel cationic hydrogels, containing basic (cationic) groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are three-dimensional polymer networks, having good water permeability and mechanical properties, and are obtained by simultaneous polymerization and crosslinking, in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) hydroxyalkyl acrylate or methacrylate, (b) a cationic monomer -- usually an ester of acrylic or methacrylic acid with an amino alcohol, the terminal amino group of which may be quaternized, such as dimethylaminoethyl methacrylate or acrylate and the quaternized derivatives thereof, and (c) a cross-linking agent, such as a glycol diacrylate or dimethacrylate; if desired there may also be present (d) one or more additional monomers, usually an acrylic monomer such as an alkyl acrylate or methacrylate, acrylamides etc. (although other monomers such as vinyl acetate, styrene, etc. may also be used) which is copolymerizable with (a), (b) and (c). The thus obtained cationic hydrogels are useful for combining, by reaction or complexing, with materials having an opposite charge; such as acidic or anionic agricultural chemicals (insecticides, herbicides, fungicides, plant growth regulators, etc.), germicides, pharmaceuticals, cosmetics, hormones, enzymes, flavors, fragrances, antiperspirants, metals and the like, both to recover such acidic or anionic materials from an aqueous medium and for purifying water containing them, and also for the preparation of a complex or other combination of the cationic hydrogel with such materials which may be useful per se or from which the complexed or combined acidic or anionic material may be slowly or controllably released.

6. 发明授权

US4049608A Functional monomers and copolymers thereof 失效
标题翻译：功能性单体及其共聚物
公开(公告)号：US4049608A
公开(公告)日：1977-09-20
申请号：US706206
申请日：1976-07-19
申请人： Robert Steckler , Fred Robinson , Robert F. Farmer, III
发明人： Robert Steckler , Fred Robinson , Robert F. Farmer, III
IPC分类号： C07C309/12 , C08F2/24 , C08L33/14
CPC分类号： C08F2/24 , C07C309/12
摘要： Novel copolymerizable esters of cinnamic acid or an .omega.-alkenoic acid of from 4 to 18 carbon atoms, such as undecylenic acid, with certain hydroxyalkane sulfonic acids, such as isethionic acid, are described together with processes of making them and copolymers thereof. These novel copolymerizable esters may be made by reaction of the .omega.-alkenoic or cinnamic acid with the hydroxyalkane sulfonic acid or a sultone, such as propane sultone. These novel ester are useful as copolymerizable surfactants in the emulsion polymerization of ethylenically unsaturated monomers; particularly for the production of self-stabilizing latices of polymeric materials possessing excellent mechanical stability and from which can be deposited films having improved adhesion, pigment wetting and bonding properties and greatly improved resistance to water. They are also useful as comonomers for the production of polymeric materials having sulfonic acid functionality, such as polyelectrolyte materials based on acrylonitrile, vinyl chloride, vinyl acetate, acrylates, methacrylates, styrene, etc.; for example, when used as a comonomer in the production of fibers and films based on the above monomers, they impart improved dye receptivity and anti-static properties to the polymeric fibers and films so made.
摘要翻译：将具有4至18个碳原子的肉桂酸或ω-链烯酸（例如十一碳烯酸）与某些羟基烷基磺酸如羟乙磺酸的新型可共聚的酯与其制备方法和其共聚物一起进行了描述。这些新型可共聚的酯可以通过ω-亚油酸或肉桂酸与羟基链烷酸磺酸或诸如丙磺酸内酯的磺内酯的反应来制备。这些新型酯可用作烯属不饱和单体的乳液聚合中的可共聚表面活性剂; 特别是用于生产具有优异的机械稳定性的聚合材料的自稳定胶粘剂，并且可以从其中提供具有改进的粘合性，颜料润湿性和粘合性能以及极大改善的耐水性的沉积膜。它们也可用作生产具有磺酸官能团的聚合物材料的共聚单体，例如基于丙烯腈，氯乙烯，乙酸乙烯酯，丙烯酸酯，甲基丙烯酸酯，苯乙烯等的聚电解质材料; 例如，当在基于上述单体的纤维和薄膜的生产中用作共聚单体时，它们赋予所制成的聚合物纤维和薄膜更好的染料接受性和抗静电性能。

7. 发明授权

US4426492A Disposable, hydrogel soft contact lenses 失效
标题翻译：一次性水凝胶软性隐形眼镜
公开(公告)号：US4426492A
公开(公告)日：1984-01-17
申请号：US298865
申请日：1981-09-03
申请人： Robert Steckler
发明人： Robert Steckler
IPC分类号： C08F8/14 , G02B1/04 , C08L29/04
CPC分类号： C08F8/14 , G02B1/043 , C08F2810/30 , Y10S525/937
摘要： Stable three dimensional hydrogels which absorb water, but are insoluble in water, and are particularly useful for the making of soft contact lenses, are prepared by reacting a water insoluble polyvinyl resin which contains reactive hydroxyl groups in its polymer chain, with a di- or poly-basic acid anhydride, to thereby introduce pendant carboxyl groups into the polymer chain, followed by treatment of the thus obtained carboxylated polymer to effect a limited amount of crosslinking thereof whereby a sparingly crosslinked hydrophilic polymer is obtained which when immersed in water absorbs water and swells to form a hydrogel, which does not dissolve in water.
摘要翻译：通过使其聚合物链中含有反应性羟基的水不溶性聚乙烯基树脂与二次或二次或多次的水溶性聚合物反应来制备吸收水但不溶于水并且特别可用于制备软性隐形眼镜的稳定的三维水凝胶聚酰胺酸酐，从而将聚合物链中的羧基引入到聚合物链中，然后处理由此得到的羧化聚合物进行有限量的交联，由此得到少量交联的亲水性聚合物，当浸入水中时，溶胀形成水凝胶，不溶于水。

8. 发明授权

US4071508A Anionic hydrogels based on hydroxyalkyl acrylates and methacrylates 失效
公开(公告)号：US4071508A
公开(公告)日：1978-01-31
申请号：US549098
申请日：1975-02-11
申请人： Robert Steckler
发明人： Robert Steckler
IPC分类号： C08F220/28 , C08F220/20
CPC分类号： C08F220/28 , Y10S514/944
摘要： Novel anionic hydrogels, containing acidic groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are stable three-dimensional polymer networks, having good water permeability and mechanical properties, and are obtained by simultaneous polymerization and cross-linking, in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) hydroxyalkyl acrylate or methacrylate, (b) a polymerizable acidic monomer containing a sulfonic acid, sulfate or phosphate group in its molecular structure, such as sulfo-ethyl acrylate or methacrylate or a sulfate or phosphate derivative of a hydroxyalkyl- acrylate or methacrylate, and (c) a cross-linking agent, such as a glycol diacrylate or dimethacrylate; if desired there may also be present (d) one or more additional monomers, usually an acryloid monomer such as an alkyl acrylate or methacrylate, acrylamides etc. (although other monomers such as vinyl acetate, styrene, etc. may also be used) which is copolymerizable with (a), (b) and (c). The thus obtained anionic hydrogels are useful for combining, by reaction or complexing, with materials having an opposite charge; such as basic or cationic agricultural chemicals (insecticides, herbicides, fungicides, plant growth regulators, etc.), germicides, pharmaceuticals, cosmetics, hormones, enzymes, flavors, fragrances, antiperspirants, metals and the like, both to recover such basic or cationic materials from an aqueous medium and for purifying water containing them, and also for the preparation of a complex or other combination of the anionic hydrogel with such materials which may be useful per se or from which the complexed or combined basic or cationic material may be slowly or controllably released.

9. 发明授权

US3532679A Hydrogels from cross-linked polymers of n-vinyl lactams and alkyl acrylates 失效
标题翻译：来自N-乙烯酰胺和丙烯酸烯丙酯的交联聚合物的水解
公开(公告)号：US3532679A
公开(公告)日：1970-10-06
申请号：US3532679D
申请日：1969-04-07
申请人： ROBERT STECKLER
发明人： STECKLER ROBERT
IPC分类号： G02B1/04 , C08F15/40
CPC分类号： G02B1/043 , C08L39/06

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