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    • 12. 发明授权
      US4212832A Production of high viscosity phosphoric and phosphonic acid aryl esters 失效
    • Production of high viscosity phosphoric and phosphonic acid aryl esters
    • 生产高粘度磷酸和膦酸芳基酯
    • US4212832A
    • 1980-07-15
    • US936987
    • 1978-08-25
    • Karl-Heinz Mitschke , Reinhard Schliebs
    • Karl-Heinz Mitschke , Reinhard Schliebs
    • C08K5/00 , C07F9/12 , C08G16/02 , C08G79/00 , C08G79/02 , C08K5/51 , C08L1/00 , C08L27/00 , C08L67/00 , C07F9/09
    • C08G16/0243
    • A process for the production of a relatively high molecular weight phosphoric or phosphonic acid aryl ester, comprising reacting a phosphoric or phosphonic acid aryl ester with formaldehyde in the presence of sulphuric acid at a temperature from about 10.degree. to 120.degree. C. Advantageously, the aryl ester is of the formula ##STR1## in which R is a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a halogen atom, an aryloxy group, or an aryl group;R.sub.1 is a group OC.sub.6 H.sub.m R.sub.n in which m+n=5, an alkyl group, a haloalkyl group or an optionally substituted aryl group;R.sub.2 is a group OC.sub.6 H.sub.m R.sub.n, in which m+n=5; andn is from 1 to 3,about 0.5 mole of formaldehyde in the form of paraformaldehyde or trioxane is employed per mole of aryl ester, about 1.5 to 2 moles of sulphuric acid are used per mole of aryl ester, the sulphuric acid is employed as a solution of at least about 95% concentration, and the reaction is effected at a temperature of about 40.degree. to 80.degree. C. in the presence of an inert solvent. The products are new and useful as flame-proofing agents in the production of laminated papers and polyesters, as fire-retarding plasticizers in plastics such as PVC, as additives to plastics such as polyphenylene oxides and also as low-flammability hydraulic oils.
    • 一种生产相对高分子量磷酸或膦酸芳酯的方法，包括在硫酸存在下，在约10-120℃的温度下使磷酸或膦酸芳基酯与甲醛反应。有利的是， 芳基酯为其中R为氢原子，具有1至6个碳原子的烷基，卤原子，芳氧基或芳基的式“IMAGE”+ TR“IMA” R1是其中m + n = 5，烷基，卤代烷基或任选取代的芳基的基团OC6HmRn; R2是OC6HmRn基团，其中m + n = 5; 并且n为1至3，每摩尔芳基酯使用约0.5摩尔以多聚甲醛或三恶烷形式的甲醛，每摩尔芳基酯使用约1.5至2摩尔硫酸，硫酸用作 至少约95％浓度的溶液，并且在约40℃至80℃的温度下在惰性溶剂的存在下进行反应。 该产品在生产层压纸和聚酯中作为阻燃剂是新型的并且是有用的，作为塑料如PVC的阻燃增塑剂，作为塑料如聚苯醚的添加剂以及低可燃性液压油。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Global Dossier Espacenet 法律信息 同族专利 专利引用
    • 16. 发明授权
      US4076763A Polysiloxane/polycarbodiimide copolymers 失效
    • Polysiloxane/polycarbodiimide copolymers
    • 聚硅氧烷/聚碳二亚胺共聚物
    • US4076763A
    • 1978-02-28
    • US758528
    • 1977-01-11
    • Karl-Friedrich Thom , Reinhard Schliebs
    • Karl-Friedrich Thom , Reinhard Schliebs
    • C08G77/00 , C08G18/10 , C08G18/61 , C08G77/42 , C08G77/458 , C08G77/48 , C08G77/54 , H01B3/46 , C08L83/00
    • C08G77/54 , C08G18/10 , C08G18/61 , C08G77/42 , C08G77/458
    • An organopolysiloxane/polycarbodiimide copolymer comprising optionally repeating structural units of the formula ##STR1## wherein R is an alkyl, alkenyl or aryl radical with up to 12 carbon atoms,R.sup.1 is an alkyl radical with up to 4 carbon atoms,R.sup.2 is a divalent hydrocarbon radical with up to 6 carbon atoms,X is oxygen or the group ##STR2## R.sup.3 is hydrogen or an alkyl, aryl, aralkyl or cycloalkyl radical with up to 8 carbon atoms,A is a divalent aromatic radical with up to about 40 carbon atoms,n is an integer from 0 to about 10,000,z is an integer from 1 to about 1500Is produced by reacting a stoichiometric excess of a diisocyanate of the formula A(NCO).sub.2 with at least one member selected from the group consisting of an .alpha.,.omega.-diaminoalkylpolysiloxane of the formula ##STR3## and an .alpha.,.omega.-dihydroxypolysiloxane of the formula ##STR4## in the presence of a carbodiimidization catalyst.
    • 一种有机聚硅氧烷/聚碳二亚胺共聚物，其包括任选地具有下式的重复结构单元：其中R是具有至多12个碳原子的烷基，烯基或芳基，R 1是具有至多4个碳原子的烷基，R 2是二价烃 具有多达6个碳原子的基团，X是氧或基团R 3是氢或具有至多8个碳原子的烷基，芳基，芳烷基或环烷基，A是具有至多约40个碳原子的二价芳族基团 ，N是从0到约10,000的整数，Z是从1到约1500的整数，通过使至少一个选自以下的组成员的组合中的至少一个成员反应式（NCO）2的二异氰酸酯的生物降解产生： α，ω-二氨基烷基聚硅氧烷和式（IMAGE）的α，ω-二羟基聚硅氧烷在碳二亚胺化催化剂存在下反应。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 18. 发明授权
      US4052484A Substituted cyclic phosphine oxides 失效
    • Substituted cyclic phosphine oxides
    • 取代的环磷酰氧化物
    • US4052484A
    • 1977-10-04
    • US648710
    • 1976-01-13
    • Reinhard Schliebs , Hans-Dieter Block
    • Reinhard Schliebs , Hans-Dieter Block
    • C07F9/53 , C07F9/6568 , C07F9/32 , C07F9/48
    • C07F9/65685
    • A cyclic phosphine oxide of the formula ##STR1## in which R.sup.1 is an alkyl or an aryl radical having up to 14 carbon atoms,R.sup.2, r.sup.3 and R.sup.4 each independently is a C.sub.1 -C.sub.4 -alkyl radical, hydrogen, chlorine or bromine,X and Y each independently is oxygen or sulfur,a, b, and c each independently is 0 or 1, andR.sup.5 is a C.sub.1 -C.sub.12 -alkyl radical and, where a = 0, also an aryl radical and, where a = 1, an equivalent of a cation,R.sup.6 is a C.sub.1 -C.sub.12 -alkyl radical and, where b = 0, also an aryl radical and, where b = 1, an equivalent of a cation,Is produced by reacting an unsaturated 5-membered cyclic phosphine oxide of the formula ##STR2## with a compound containing a phosphorus-hydrogen bond and of the formula ##STR3## in which R.sup.7 is a C.sub.1 -C.sub.12 -alkyl radical or, where a = 0, also an aryl radical, andR.sup.8 is a C.sub.1 -C.sub.12 -alkyl radical or, where b = 0, also an aryl radical,In the presence of free radicals at a temperature of about 50.degree. C to about 300.degree. C, and the reaction product is optionally hydrolyzed and converted into a salt.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 19. 发明授权
      US4043977A Non-stick polyorganosiloxane coating compositions 失效
    • Non-stick polyorganosiloxane coating compositions
    • 不粘聚有机硅氧烷涂料组合物
    • US4043977A
    • 1977-08-23
    • US670583
    • 1976-03-25
    • Armand deMontigny , Kurt-Wilhelm Eichenhofer , Hans Toepsch , Reinhard Schliebs
    • Armand deMontigny , Kurt-Wilhelm Eichenhofer , Hans Toepsch , Reinhard Schliebs
    • C08L83/00 , C08G77/04 , C08K5/34 , C08L83/04 , C08L83/07 , C09D183/04 , D06M15/643 , D21H19/00 , D21H19/32
    • D21H19/32 , C08G77/045 , C08L83/04 , D06M15/6436 , C08G77/12 , C08G77/20 , C08G77/70 , Y10T428/31663
    • A composition for coating paper, films and fiber materials, comprisingA. 4 parts by weight of a linear polyorganosiloxane with ends stopped by vinyl groups and having a viscosity of up to about 500 cP (20.degree. C) andB. about 0.5 to 1.5 parts by weight of a crosslinking agent containing Si-vinyl units and SiH units and comprising molecules with a maximum of about 10 Si atoms bonded to one another via oxygen, and wherein the two reactive groups are present in adjacent positions in one and the same molecule and the remaining valencies of the Si atom are saturated by methyl groups and the SiH groups are present in a ratio of about 1:1 to 2.5:1 to the total amount of all Si-vinyl units present in the composition,C. a platinum metal complex, the amount of metal being up to about 0.01 part by weight -- based on 100 parts by weight of total composition, andD. a diaziridine, the amount of diaziridine being about 75 to 250 times the weight of metal.The compositon has a viscosity of about 150 cP -- the increase of the initial viscosity over a period to of at least 24 hours being less than 1 cP -- easy application from existing equipment.The present invention relates to a coating agent based on polyorganosiloxanes which is suitable for the manufacture on non-stick films or coatings on paper, films, fabric tapes and similar materials, without the use of solvents.The application of non-stick polysiloxane coatings from water or organic solvents onto paper or similar materials has in itself been known for a long time (compare, for example, Noll, Chemie und Technologie der Silicone (Chemistry and Technology of the Silicones), 2nd edition, 1968, Verlag Chemie, Weinheim, page 520) and is extensively carried out in industry. The apparatuses suitable for the application of such coatings are in general designed to apply a coating material which contains solvent and are therefore adjusted to deal with viscosities of less than 150 cP or even of less than 100 cP. Such low viscosities have the advantage that they can be adjusted very precisely by means of the solvent. In addition, dilute solutions can be processed better, and the substrate is generally wetted better. In spite of these advantages, such coating systems containing solvents still suffer from considerable shortcomings. The main disadvantage is that about 92-97% of the mixture applied must again be removed. This requires high expenditure of energy. Furthermore, for reasons of protection of the environment and reasons of profitability, it is necessary either to recover the solvent removed in this way or, if recovery is not possible, to destroy the solvent, for example by combustion. However, this requires considerable expenditure on energy or apparatuses in every case.For these reasons there has been a constantly increasing demand for a coating without solvents, but of course it is a prerequisite that with a solvent-free coating system the advantage must not be achieved at the expense of a series of other disadvantages. Admittedly, some processes have already been disclosed (compare, for example, DT-OS (German Published Specification) No. 2,210,380 and DT-OS (German Published Specification No.) 2,321,879), in which the attempt to manage without solvents has been made. However, these systems in every case still suffer from a series of disadvantages so that they are unable satisfactorily to fulfil the demands made of them. Above all, it is in respect of their viscosity behavior -- such systems are required to have a high degree of constancy of the viscosity -- that the previously known systems have only been partially satisfactory.A further aspect of the viscosity problem which also still awaits a satisfactory solution in spite of the previously known processes and compositions is the initial viscosity.As is known to those skilled in the art, a mixture of a siloxane polymer with a crosslinking agent cannot directly be brought to a lower viscosity by shortening the siloxane chains of the polymer. Short-chain rubber molecules give a hard, crumbly film of low suppleness and poor mechanical properties. Applied to paper coating, this means that the film is not abrasion-resistant, and the inadequate abrasion resistance does not necessarily relate to the breaking of the bond between the substrate and the film but to the film itself breaking. Hence it is not surprising that all examples in the known publications relate to polymers of which the viscosity is in part many times higher than 150 cP.Accordingly, it is the object of the present invention to provide a coating system or coating process which makes it posible to achieve, by means of the applicator units of the state of the art, thin, commercially acceptable films of which the uniformity and mechanical properties are such as to give constant release properties and migration properties which meet practical requirements. In detail, this means that such a process must resort to compositions which in spite of the low initial viscosities are able to give films which withstand mechanical strain and repel adhesives, while the original viscosity must remain constant for at least 24 hours under conditions resembling those encountered in practice.This object is realized in accordance with the present invention pursuant to which there is provided a composition for coating paper, films and fiber materials, comprisinga. 4 parts by weight of a linear polyorganosiloxane with ends stopped by vinyl groups and having a viscosity of up to about 500 cP (20.degree. C),b. about 0.5 to 1.5 parts by weight of a crosslinking agent containing Si-vinyl units and SiH units, comprising molecules with a maximum of about 10 Si atoms bonded to one another via oxygen, and wherein the two reactive groups are present in adjacent positions in one and the same molecule and the remaining valencies of the Si atom are saturated by methyl groups and the SiH groups are present in a ratio of 2.5:1 to the total amount of all Si-vinyl units present in the composition,c. a platinum metal complex, the amount of metal being up to about 0.01 part by weight - based on 100 parts by weight of the composition, andd. a diaziridine, the amount of diaziridine being about 75 to 250 times the weight of metal.Accordingly, it was possible to achieve the present object by making 4 parts by polyorganosiloxane with ends stopped by vinyl groups and having a viscosity of at most 500 cP/20.degree. C with 0.5 to 1.5 parts of a crosslinking agent carrying Si-vinyl groups and SiH groups; the molecular size of the crosslinking agent should not exceed 10 Si atoms which are bonded via oxygen and of which the remaining valencies are saturated by methyl groups, where they are not occupied by the above reactive groups, and the viscosity of the polyorganosiloxane is so chosen that it is more than 50 cP and that the viscosity of the total mixture does not exceed 150 cP. The SiH:Si-vinyl ratio in the mixture may vary between the ratios of 1:1 and 2.5:1. The crosslinking agent used is such that it consists of one type of molecule and carries, in addition to SiH groups, a sufficient number of Si-vinyl groups that the above conditional ratios are observed.While the linear polyorganosiloxane has a viscosity which may be as high as 500 cP/20.degree. C, it is blended with such an amount of crosslinking agent that the overall composition has a viscosity from about 50 to 150 cP/20.degree. C.In the sense of the invention, polyorganosiloxanes with ends stopped by vinyl groups are polydiorganosiloxanes which terminate in CH.sub.2 .dbd.CH-Si(CH.sub.3).sub.2 O.sub.1/2 units and of which the organo groups consist to the extent of at least about 70 % of methyl groups, the remainder optionally consisting of higher alkyl groups, preferably containing up to about 6 carbon atoms, or phenyl groups. The viscosity of these polymers, which can be prepared easily according to the state of the art, should not be less than about 50 cP. Now the upper limit of viscosity is determined by the total viscosity of the mixture, which should be less than 150 cP; accordingly, the polymer viscosity should not significantly exceed a value of 500 cP.The crosslinking agent consists, for example, of a co-hydrolysate which contains both vinyl-Si and H-Si groups in the same molecule. The following compounds would be typical representatives of this category of crosslinking agent, for example with the chain length remaining the same:(CH.sub.3).sub.3 SiOX.sub.n Y.sub.n' Si(CH.sub.3).sub.3(ch.sub.3).sub.3 siOX.sub.n Y.sub.n' Si(CH.sub.3).sub.2 H(ch.sub.3).sub.3 siOX.sub.n Y.sub.n' Si(CH.sub.3).sub.2 CH.dbd.CH.sub.2ch.sub.2 .dbd.ch(ch.sub.3).sub.2 siOX.sub.n Y.sub.n' Si(CH.sub.3).sub.2 CH.dbd.CH.sub.2ch.sub.2 .dbd.ch(ch.sub.3).sub.2 ox.sub.n Y.sub.n' Si(CH.sub.3).sub.2 HandHSi(CH.sub.3).sub.2 OX.sub.n Y.sub.n' Si(CH.sub.3).sub.2 Hwherein ##STR1## n+n' is at most about 8.These compounds are readily available and are obtained in high yields by co-hydrolysis according to the state of the art. In principle, the crosslinking agent would be allowed to possess more than 10 Si atoms bonded via O without the crosslinking reaction or the properties of the film being impaired. However, it is to be borne in mind that this would increase the viscosity of the crosslinking agent and hence also the viscosity of the mixture. In order to counteract this effect brought about by the crosslinking agent the polymer would have to be made correspondingly short. In the viscosity ranges concerned, which are in any case already low, this would not be of advantage since an over-drastic shortening of the chains would be at the expense of the mechanical properties. It has been found that the film which results from the mixture described above adheres well to its substrate, is abrasion-resistant and exhibits perfect release properties and migration properties.It is a further characteristic of the present invention that Pt catalyst known from the literature, such as the reaction product of H.sub.2 PtCl.sub.6 with octanol (Lamoreaux catalyst) or Pt compounds such as have been disclosed, for example, in DT-OS (German Published Specification No.) 2,251,297 (the disclosure of which is incorporated herein by reference) are deactivated by bringing them into contact, at room temperature, with a diaziridine of the formula ##STR2## whereinR.sub.1 and R.sub.2 represent a radical which contains up to6 C atoms (for example an alkyl radical) and whereinR.sub.1 + R.sub.2 can together form a ring system. Examples of both liquid and solid diaziridines which can be used for this purpose are dimethyldiaziridine, methylethyldiaziridine, diethyldiaziridine, methylisopropyldiaziridine, methylpropyldiaziridine, dipropyldiaziridine, pentamethylenediaziridine and hexamethylenediaziridine. The reaction is best carried out "in situ", that is to say a sufficient amount of diaziridine is added to the polymer with ends stopped by vinyl groups and the platinum catalyst is then added. It has been found that up to about 100, preferably about 10 to 12 ppm, of Pt, relative to the total amount, suffice for catalysis so that reliable curing is achieved at temperatures between 120.degree. and 150.degree. C.As can furthermore be shown in the examples which follow, good deactivation of the catalyst is achieved if the amount of diaziridine added is up to about 250 times the amount of Pt. The amount of diaziridine should not be significantly less than 75 times the amount of the Pt catalyst since in that case an increase in viscosity of 5 cP is already found over a period of 24 hours. If the diaziridine content is well matched to the amount of Pt catalyst, pot lives of over 120 hours can be achieved, without difficulties, under conditions resembling practical requirements. A main advantage of the low viscosity is that it permits the application of thin, economical films.At this point it should further be mentioned that the delaying action of the reaction products of platinum complexes with diaziridines need not be restricted to systems of low viscosity such as those described here.
    • 一种用于涂布纸，薄膜和纤维材料的组合物，包括A. 4通过乙烯基团停止并具有高达约500 CP（20℃）和B的粘度的直链多聚硅氧烷的重量的组分。约0.5至1.5 包含Si-乙烯基单元和SiH单元并含有最多约10个Si原子的分子通过氧彼此键合的交联剂的重量份数，并且其中两个反应性基团存在于同一分子中的相邻位置 并且Si原子的剩余价数被甲基饱和，并且SiH基以与组合物中存在的全部Si-乙烯基单元的总量的比例为约1:1至2.5:1存在.C.A铂 金属复合物，金属含量高达0.01重量份 - 以100重量份的总组成，D。DIAZIRIDINE，DIAZIRIDINE的量约为75至250次金属重量。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
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